2-(4-Bromo­phen­oxy)-3-isopropyl-5,6,7,8-tetra­hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

Hong-Mei Wang; Li-Li Chen; Ting Hu; Xiao-Hua Zeng

doi:10.1107/S160053680803732X

. 2008 Nov 22;64(Pt 12):o2404. doi: 10.1107/S160053680803732X

2-(4-Bromophenoxy)-3-isopropyl-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

Hong-Mei Wang ^a, Li-Li Chen ^a, Ting Hu ^a, Xiao-Hua Zeng ^a,^*

PMCID: PMC2960130 PMID: 21581373

Abstract

In the title compound, C₁₉H₁₉BrN₂O₂S, the central thienopyrimidine ring system is essentially planar, with a maximum displacement of 0.068 (3) Å. The attached cyclohexene ring adopts a half-chair conformation. The molecular conformation and crystal packing are stabilized by three intramolecular C—H⋯O hydrogen bonds and two C—H⋯π interactions.

Related literature

For background to the use of pyrimidine derivatives as drugs, see: Ding et al. (2004 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For a related structure, see: Zeng et al. (2006 ▶).

Experimental

Crystal data

C₁₉H₁₉BrN₂O₂S
M _r = 418.32
Monoclinic,
a = 13.3957 (7) Å
b = 5.7366 (3) Å
c = 13.3956 (7) Å
β = 115.5410 (10)°
V = 928.81 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 298 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.652, T _max = 0.800
5798 measured reflections
3228 independent reflections
2346 reflections with I > 2σ(I)
R _int = 0.106

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.204
S = 1.07
3228 reflections
228 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 7.69 e Å⁻³
Δρ_min = −2.63 e Å⁻³
Absolute structure: Flack (1983 ▶), 1424 Freidel pairs
Flack parameter: 0.00 (8)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803732X/at2674sup1.cif

e-64-o2404-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803732X/at2674Isup2.hkl

e-64-o2404-Isup2.hkl^{(158.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1	0.98	2.20	2.726 (10)	112
C12—H12B⋯O2	0.96	2.43	2.915 (13)	111
C13—H13A⋯O2	0.96	2.38	2.951 (10)	117
C12—H12A⋯Cg1ⁱ	0.96	2.92	3.854 (11)	165
C12—H12A⋯Cg2ⁱ	0.96	2.71	3.434 (11)	133

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Symmetry code: (i) Inline graphic . Cg1 and Cg2 are the centroids of the thiophene (S1/C5–C8) and pyrimidine (N1/N2/C7–C10) rings, respectively.

Acknowledgments

We gratefully acknowledge financial support of this work by the Research Foundation for Students and Teachers of Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

supplementary crystallographic information

Comment

Pyrimidine derivatives are attracting the increasing attention of synthetic community because of the important role played by such systems in many natural products, antibiotics and drugs (Ding et al., 2004). In recent years, we have been engaged in the preparation of the derivatives of heterocycles via aza-Wittig reaction. The title compound, (I), was synthesized and structurally characterized in this context.

The molecular structure indicates that the thieno[2,3-d]pyrimidine moiety is a conjugated system (Fig. 1). All ring atoms in thieno[2,3-d]pyrimidine are essentially coplanar (Zeng et al., 2006). The bond lengths and angles are within experimental error, in the ranges of values in previously reported structures in the Cambridge Structural Database (Version 5.26; Allen, 2002).

The cyclohexene ring adopts a half-chair conformation. The crystal packing is stabilized by three intramolecular C—H···O hydrogen bonds and two C—H···π interactions (Table 1). There exist no intermolecular hydrogen bonding interactions and no π-π stackings.

Experimental

To a solution of iminophosphorane (1.45 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added iso-propyl isocyanate (3 mmol) under dry nitrogen at room temperature. After the reaction mixture was left unstirred for 48 h at room temperature, the solvent was removed off under reduced pressure and ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed, and the residue was dissolved in CH₃CN (15 ml). After adding 4-Br-PhOH (3.1 mmol) and excess K₂CO₃ to the solution of carbodiimide, The mixture was stirred for 24 h at room temperature, the solution was condensed and the residue was recrystallized by EtOH to give the title compound, (I), in yield of 80% (m.p. 478 K). Elemental analysis calculated for C₁₉H₁₉BrN₂O₂S: C 54.42, H 4.57, N 6.68. Found: C 54.56, H 4.42, N 6.53. Crystals suitable for single crystal X-ray diffraction were obtained by vapor diffusion of hexane and dichloromethane (1:3 v/v) at room temperature.