7-Benzyl-2-[(cyclo­propyl­meth­yl)amino]-3-phenyl-5,6,7,8-tetra­hydro­pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one

Hong Chen

doi:10.1107/S1600536811029771

. 2011 Jul 30;67(Pt 8):o2191. doi: 10.1107/S1600536811029771

7-Benzyl-2-[(cyclopropylmethyl)amino]-3-phenyl-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one

Hong Chen ^a,^*

PMCID: PMC3213622 PMID: 22091199

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₂₆H₂₆N₄OS. In each molecule, the thienopyrimidine fused-ring system is essentially planar with a maximum deviation of 0.0409 (18) for the N atom. In one molecule, this ring system forms diherdral angles of 84.8 (1) and 67.6 (1)° with the adjacent phenyl and benzyl rings, respectively, while the corresponding angles in the other molecule are 77.9 (1) and 66.5 (1)°.

Related literature

For the biological activity of thienopyrimidine-containing compounds, see: Amr et al. (2010 ▶); Huang et al. (2009 ▶); Jennings et al. (2005 ▶); Kikuchi et al. (2006 ▶); Mavrova et al. (2010 ▶); Santagati et al. (2002 ▶). For related structures, see: Xie et al. (2008 ▶); Hu et al. (2007 ▶).

Experimental

Crystal data

C₂₆H₂₆N₄OS
M _r = 442.58
Orthorhombic,
a = 18.269 (5) Å
b = 27.564 (7) Å
c = 18.115 (5) Å
V = 9122 (4) Å³
Z = 16
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 296 K
0.23 × 0.19 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.962, T _max = 0.975
92541 measured reflections
10442 independent reflections
7717 reflections with I > 2σ(I)
R _int = 0.067

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.157
S = 1.06
10442 reflections
577 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029771/lh5288sup1.cif

e-67-o2191-sup1.cif^{(36.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029771/lh5288Isup2.hkl

e-67-o2191-Isup2.hkl^{(510.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029771/lh5288Isup3.cml

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

Acknowledgments

This work was supported financially by the Science Foundation of Hubei Province Education Department, China (project No. D20091301) and the Excellent Fund for Scientific Research and Special Projects in China Three Gorges University, China (project No. KJ2009B004).

supplementary crystallographic information

Comment

Derivatives of heterocycles containing the thienopyrimidine system have proved to show significant antifungal, antibacterical, anticonvulsant and angiotensin antagonistic activities (Amr et al. 2010; Huang et al. 2009; Jennings et al. 2005; Kikuchi et al. 2006; Mavrova et al. 2010; Santagati et al. 2002). Recently, we have focused on the synthesis of fused heterocyclic systems containing thienopyrimidine via aza-wittig reactions under mild conditions. Some examples of crystal structures of fused pyrimidinone derivatives have been reported (Xie et al., 2008; Hu et al., 2007). The title compound (I) has potential use as a precursor for obtaining bioactive molecules with fluorescence properties. Herein, we report the crystal structure of (I).

The asymmetric unit of the title compound is shown in Fig. 1. There are two crystallographically independent molecules per asymmetric unit. In each, the thienopyrimidine fused ring system is essentially planar. In one molecule this ring system forms diherdral angles of 84.8 (1) and 67.6 (1) ° with the adjacent phenyl (C17-22) ring and benzyl phenyl ring (C1-C6), respectively, and the corresponding angles in the other molecule are 77.9 (1)° for C43-C48 and 66.5 (1)° for C28-C32.

Experimental

A schematic of the synthesis is given in Fig. 2. 1-Isocyanatobenzene (2 mmol) under nitrogen atmosphere was added to a solution of iminophosphorane (2 mmol) in anhydrous CH₂Cl₂ (10 ml) at room temperature. When the reaction mixture was left unstirred for 12 h at 273-278K, iminophosphorane was added (TLC monitored). The solvent was removed under reduced pressure and ether/petroleum ether (volume ratio 1:2, 20 ml) was added to precipitate triphenylphosphine oxide. Removal of the solvent gave the carbodiimide, which was used directly without further purification. Cyclopropylmethanamine (2 mmol) was added to the solution of carbodiimide in anhydrous dichloromethane (10 ml). After the reaction mixture was left unstirred for 5–6 h, the solvent was removed and anhydrous EtOH (10 ml) with several drops of EtONa (in EtOH) was added to the mixture. The mixture was stirred for another 6–8 h at room temperature. The solution was condensed and the residual was recrystallized from EtOH to give the expected title compound as white crystals.