Startseite Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
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Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3

  • Wuji Sun ORCID logo , Lixin Sun und Hong Yan EMAIL logo
Veröffentlicht/Copyright: 20. Juni 2024

Abstract

C26H22BrN3O3, monoclinic, P21/c (no. 14), a = 17.7467(15) Å, b = 10.7974(8) Å, c = 11.9136(8) Å, β = 96.084°, V = 2270.0(3) Å3, Z = 4, Rgt (F) = 0.0375, wRref (F 2) = 0.1205, T = 293 K.

CCDC no.: 2350232

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.25 × 0.23 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.85 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 26,554, 3,990, 0.052
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3,133
N(param)refined: 300
Programs: Bruker, 1 SHELX 2 , 3
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
Br1 0.88233 (2) −0.02634 (3) 0.99632 (3) 0.08232 (18)
C1 0.84729 (13) 0.0981 (2) 0.89158 (19) 0.0480 (5)
C2 0.80088 (15) 0.0615 (3) 0.7965 (2) 0.0569 (6)
H2 0.788148 −0.021486 0.785856 0.068*
C3 0.77382 (14) 0.1479 (3) 0.7184 (2) 0.0585 (7)
H3 0.742727 0.123915 0.654327 0.070*
C4 0.79299 (14) 0.2710 (3) 0.7353 (2) 0.0533 (6)
H4 0.773879 0.329921 0.682881 0.064*
C5 0.84016 (13) 0.3074 (2) 0.82895 (19) 0.0474 (5)
H5 0.853412 0.390472 0.837892 0.057*
C6 0.86833 (12) 0.2216 (2) 0.91054 (17) 0.0406 (5)
C7 0.92939 (12) 0.3623 (2) 1.06037 (17) 0.0395 (5)
C8 0.99197 (14) 0.4675 (2) 1.2043 (2) 0.0509 (6)
H8 1.025998 0.469589 1.269212 0.061*
C9 0.95853 (13) 0.5762 (2) 1.16860 (18) 0.0481 (6)
H9 0.969378 0.651087 1.205361 0.058*
C10 0.90707 (12) 0.5661 (2) 1.07316 (17) 0.0400 (5)
C11 0.81285 (13) 0.6552 (2) 0.94275 (18) 0.0437 (5)
C12 0.82842 (14) 0.6845 (2) 0.8353 (2) 0.0498 (6)
H12 0.877187 0.707039 0.821681 0.060*
C13 0.77079 (14) 0.6800 (2) 0.7480 (2) 0.0495 (6)
H13 0.781488 0.698303 0.675054 0.059*
C14 0.69701 (13) 0.6487 (2) 0.76656 (19) 0.0448 (5)
C15 0.68371 (14) 0.6195 (2) 0.8763 (2) 0.0521 (6)
H15 0.635029 0.597460 0.890928 0.063*
C16 0.74112 (14) 0.6223 (2) 0.9645 (2) 0.0522 (6)
H16 0.731238 0.602169 1.037369 0.063*
C17 0.63315 (14) 0.6485 (2) 0.6779 (2) 0.0495 (6)
H17 0.585181 0.653871 0.702264 0.059*
C18 0.63530 (14) 0.6417 (2) 0.5672 (2) 0.0503 (6)
H18 0.682696 0.636365 0.540920 0.060*
C19 0.56841 (14) 0.6418 (2) 0.48257 (19) 0.0493 (6)
C20 0.49824 (14) 0.6819 (2) 0.50969 (18) 0.0506 (6)
H20 0.493203 0.712757 0.581390 0.061*
C21 0.43554 (15) 0.6758 (2) 0.4293 (2) 0.0517 (6)
C22 0.44241 (15) 0.6316 (3) 0.3228 (2) 0.0541 (6)
H22 0.400093 0.627162 0.269814 0.065*
C23 0.51149 (15) 0.5943 (2) 0.29503 (19) 0.0518 (6)
C24 0.57548 (14) 0.5988 (2) 0.3740 (2) 0.0531 (6)
H24 0.622375 0.573392 0.354193 0.064*
C25 0.35050 (17) 0.7496 (4) 0.5553 (2) 0.0760 (9)
H25A 0.363408 0.684629 0.608923 0.114*
H25B 0.297893 0.770332 0.555396 0.114*
H25C 0.380933 0.821308 0.575679 0.114*
C26 0.5809 (2) 0.5067 (3) 0.1525 (3) 0.0817 (9)
H26A 0.618187 0.571345 0.161651 0.123*
H26B 0.573217 0.482536 0.074552 0.123*
H26C 0.598196 0.436667 0.197735 0.123*
N1 0.91724 (12) 0.25094 (18) 1.00624 (15) 0.0496 (5)
H1 0.943712 0.190136 1.035664 0.059*
N2 0.89218 (10) 0.46201 (17) 1.01814 (15) 0.0398 (4)
N3 0.97961 (11) 0.35833 (19) 1.15302 (16) 0.0493 (5)
O1 0.86971 (9) 0.66936 (15) 1.03381 (14) 0.0529 (4)
O2 0.36393 (10) 0.7099 (2) 0.44802 (15) 0.0708 (6)
O3 0.51207 (13) 0.5501 (2) 0.18695 (16) 0.0735 (6)

1 Source of material

Pterostilbene (256 mg, 1 mmol) and 1,4-dioxane (20 mL) were added in a solution of sodium hydroxide (40 mg, 1 mmol) in water (10 mL) and the mixture was maintained at ice-bath temperature. To this was added, dropwise, a solution of 2,4-dichloroprymidine (149 mg, 1 mmol) in 1,4-dioxane (20 mL). The reaction was monitored by thin layer chromatography (TLC, petroleum ether:ethyl acetate = 4:1, v/v). When the reaction was completed, the mixture was concentrated under vacuum and recrystallized from ethyl acetate. The intermediate (E)-2-chloro-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidine was obtained as a white soild. The intermediate (368 mg, 1 mmol) and 2-bromoaniline (172 mg, 1 mmol) were dissolved in isopropyl alcohol (10 mL), and concentrated hydrochloric acid (2–3 drops) was added. The reaction mixture was reacted at reflux temperature for 4 h. After the reaction was finished, the mixture was concentrated under reduced pressure and extracted with ethyl acetate (30 mL). The organic layer was washed with brine (25 mL × 3), dried, filtered and concentrated. The residue was purified by recrystallization (ethyl acetate). The crystals of the title compound were grown by slow evaporation of its dichloromethane:n-hexane (1:2, v/v) solution at room temperature.

2 Experimental details

All hydrogen atoms were placed in the calculated positions and all the non-hydrogen atoms were refined anisotropically.

3 Comment

Pterostilbene, chemically related to resveratrol, is not only an active phytonutrient but also a potential drug with multiple biomedical applications. 4 8 In this paper, we report the synthesis and crystal structure of a novel pterostilbene compound with a pyrimidine fragment. Single-crystal structure analysis reveals that there is one molecule in the asymmetric unit (cf. figure). Its molecular structure contains a pyrimidine ring, three benzene rings, a carbon–carbon double bond and two methoxy groups. The pyrimidine ring and two benzene rings are linked by N(1) atom and O(1) atom. The two benzene rings are linked by the carbon–carbon double bond. The carbon-carbon double bond and the attached benzene rings are also approximately coplanar, while the dihedral angle of the two benzene rings is 37.93°. The two methoxy groups (C21–O2–C25 and C23–O3–C26) are in the same plane as their attached benzene ring and their dihedral angles to the attached benzene ring are 3.09 and 1.21°, respectively. The torsion angles of C6–N1–C7 and C10–O1–C11 are 129.56 and 117.45°. All bond angles and lengths are within the normal range. 9 And the structural characteristics of the title compound are similar to those of N-phenyl-4-(4-(2-(2-pyridinyl)ethenyl)phenoxy)picolinamide 10 and (E)-4-(6-(4-(2-(pyridin-4-yl)vinyl)phenoxy)pyrimidin-4-yl)morpholine. 11

The complete set of X-ray diffraction data for the title compound was deposited to the Cambridge Crystallographic Data Centre (CCDC entry no. 2350232).


Corresponding author: Hong Yan, College of Chemistry and Life Science, Beijing University of Technology, 100124 Beijing, P.R. China, E-mail:

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

  3. Research funding: None declared.

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Received: 2024-04-27
Accepted: 2024-05-30
Published Online: 2024-06-20
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O )cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O :O ,O )-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 )
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N -dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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