7-(Benzyl­sulfan­yl)-5-(2-methoxy­phen­yl)-1,3-dimethyl-5,6-dihydro­pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Ayoob Bazgir; Fereshteh Faraji

doi:10.1107/S160053680802401X

. 2008 Aug 6;64(Pt 9):o1666. doi: 10.1107/S160053680802401X

7-(Benzylsulfanyl)-5-(2-methoxyphenyl)-1,3-dimethyl-5,6-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Ayoob Bazgir ^a,^*, Fereshteh Faraji ^b

PMCID: PMC2960738 PMID: 21201659

Abstract

In the molecule of the title compound, C₂₂H₂₂N₄O₃S, the benzene and phenyl rings are oriented at a dihedral angle of 88.72 (4)°. The other two rings have flattened-boat conformations. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules.

Related literature

For general background, see: Sharma et al. (2004 ▶); Quiroga et al. (2002 ▶); Devi et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₂H₂₂N₄O₃S
M _r = 422.51
Monoclinic,
a = 10.9216 (9) Å
b = 8.8528 (5) Å
c = 20.7263 (15) Å
β = 90.638 (6)°
V = 2003.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 294 (2) K
0.4 × 0.3 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T _min = 0.928, T _max = 0.985
23191 measured reflections
5394 independent reflections
4510 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.135
S = 1.15
5394 reflections
278 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802401X/hk2501sup1.cif

e-64-o1666-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802401X/hk2501Isup2.hkl

e-64-o1666-Isup2.hkl^{(258.8KB, 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
N4—H4B⋯O1ⁱ	0.85 (3)	2.02 (3)	2.836 (2)	161 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

AB is grateful to the Islamic Azad University, Dorood Branch, for financial support.

supplementary crystallographic information

Comment

The importance of fused pyrimidines, common source for the development of new potential therapeutic agents (Sharma et al., 2004), is well known. Among them, the pyrimido[2,3-d]pyrimidines are an important class of annulated uracils with biological significance because of their connection with purine pteridine system (Quiroga et al., 2002). Numerous reports delineate the antitumor, antivial, antioxidant, antifungal and hepatoprotective activities of these compounds (Devi et al., 2003). Therefore, for the preparation of these complex molecules large efforts have been directed towards the synthetic manipulation of uracils. We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and D (C16-C21) are, of course, planar and they are oriented at a dihedral angle of A/D = 88.72 (4)°. Rings B (N2/N3/C9/C11/C13/C14) and C (N1/N4/C8/C9/C14/C15) have flattened-boat [φ = 105.63 (2)°, θ = 100.53 (3)° (for ring B) and φ = 29.58 (3)°, θ = 58.23 (3)° (for ring C)] conformations, having total puckering amplitudes, Q_T, of 0.120 (3) and 0.364 (3) Å, respectively (Cremer & Pople, 1975).

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, 6-amino-1,3-dimethyluracil (0.15 g, 1 mmol), 2-methylbenzaldehyde (0.12 g, 1 mmol), 2-benzylthiourea hydrochloride (0.30 g, 1.5 mmol) and p-toluenesulfonic acid (0.1 g) were mixed. The reaction mixture was placed in a screw capped vial and irradiated for 5 min with a power of 700 W microwave irradiation. After cooling, the reaction mixture was washed with water, and then recrystallized from ethyl acetate to afford the title compound (yield; 0.25 g. 65%, m.p. 519-521 K).