2-(Dibutyl­amino)-3-(4-fluoro­phen­yl)-5,6,7,8-tetra­hydro-7-methyl-6,8-di­phenyl­pyridine­[3′,4′:2,3]thieno[5,4-d]pyrimidin-4(3H)-one

Guo-ping Zeng; Qing Li; Yang-gen Hu

doi:10.1107/S1600536808002845

. 2008 Jan 30;64(Pt 2):o535. doi: 10.1107/S1600536808002845

2-(Dibutylamino)-3-(4-fluorophenyl)-5,6,7,8-tetrahydro-7-methyl-6,8-diphenylpyridine[3′,4′:2,3]thieno[5,4-d]pyrimidin-4(3H)-one

Guo-ping Zeng ^a, Qing Li ^b, Yang-gen Hu ^c,^*

PMCID: PMC2960238 PMID: 21201554

Abstract

In the crystal structure of the title compound, C₃₆H₃₉FN₄OS, the two fused rings of the thienopyrimidine system are coplanar. The 4-fluorophenyl ring is twisted with respect to the heterocyclic pyrimidinone ring by 67.21 (14)°. The piperidine ring shows a half-chair conformation. One of the n-butyl chains is disordered equally over two sites. The crystal packing is stabilized by C—H⋯O hydrogen bonds.

Related literature

The preparation and biological activity are described by Walter (1999a ▶,b ▶). For related literature, see: Ding et al. (2004 ▶). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C₃₆H₃₉FN₄OS
M _r = 594.77
Monoclinic,
a = 13.723 (4) Å
b = 9.836 (3) Å
c = 24.5496 (15) Å
β = 101.342 (2)°
V = 3249.0 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 294 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.973, T _max = 0.986
32225 measured reflections
6359 independent reflections
4457 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.075
wR(F ²) = 0.178
S = 1.10
6359 reflections
420 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536808002845/bt2671sup1.cif

e-64-0o535-sup1.cif^{(30.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002845/bt2671Isup2.hkl

e-64-0o535-Isup2.hkl^{(311.3KB, 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
C4—H4⋯O1ⁱ	0.93	2.47	3.304 (6)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (grant No. D200724001) and the Science Research Project of Yunyang Medical College (grant No. 2006QDJ16).

supplementary crystallographic information

Comment

The derivatives of heterocycles containing the thienopyrimidine system, which are well known bioisosteres of quinazolines, are of great importance because of their remarkable biological properties (Walter, 1999a; Walter, 1999b; Ding et al., 2004). Recently, we have focused on the synthesis of the fused heterocycle systems containing thienopyrimidine via aza-Wittig reaction at room temperature. Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Hu et al., 2006; 2007). The title compound (Fig. 1) may be used as a precursor for obtaining bioactive molecules. The two fused rings of the thienopyrimidine ring system are coplanar, making a dihedral angle of 0.36 (13)°. The p-fluorophenyl ring is twisted with respect to pyrimidinone ring by 67.21 (14)°. The piperidine ring shows a half-chair conformation [φ =25.9 (4)° and θ = 49.9 (3)°, puckering Amplitude = 0.515 (3) Å]. One of the n-butyl chains is disordered over two sites. The crystal packing is stabilized by C—H···O hydrogen bonds interactions (Table 1).

Experimental

To a solution of ethyl 2-((p-flurophenylimino)methyleneamino)-4,5,6,7-tetrahydro-6-methyl- 5,7-diphenylthieno[2,3-c]pyridine-3-carboxylate (3 mmol) in dichloromethane (5 ml) was added dibutylamine (3 mmol). After stirring the reaction mixture for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 4 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from dichloromethane and ethanol (v/v = 1:1) to give the title compound in a yield of 80%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:3 v/v) at room temperature.