4,5,8a-Triphenyl­perhydro­pyrimido[4,5-d]pyrimidine-2,7-dione monohydrate

Yulin Zhu; Wanhong Qiu; Fufen Yang; Guichan Li

doi:10.1107/S1600536810019525

. 2010 May 29;66(Pt 6):o1503. doi: 10.1107/S1600536810019525

4,5,8a-Triphenylperhydropyrimido[4,5-d]pyrimidine-2,7-dione monohydrate

Yulin Zhu ^a,^*, Wanhong Qiu ^a, Fufen Yang ^a, Guichan Li ^a

PMCID: PMC2979643 PMID: 21579563

Abstract

The title compound, C₂₄H₂₂N₄O₂·H₂O, was synthesized by the trimethylchlorosilane-catalysed reaction between urea, benzaldehyde and acetophenone. The organic molecule comprises two fused tetrahydropyrimidinone rings with phenyl substituents at the 4- and 5-positions on the tetrahydropyrimidinone rings and a third phenyl substituent at the ring junction 8-position. The 4- and 5-substituted phenyl rings are inclined at a dihedral angle of 22.72 (11)° to one another and make angles of 47.95 (7) and 65.76 (7)° with the third phenyl substituent. In the crystal structure, intermolecular N—H⋯O contacts link pyrimido[4,5-d]pyrimidine molecules into centrosymmetric dimers. Additional N—H⋯O and O—H⋯O hydrogen bonds involving the water molecule generate a three-dimensional network.

Related literature

For the therapeutic and pharmacological properties of pyrimidopyrimidines, see: Agarwal et al. (2005 ▶); Gangjee et al. (2005 ▶). For the synthesis of related compounds, see: Shi et al. (2007 ▶); Zhu et al. (2005 ▶). For reference bond-length data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₄H₂₂N₄O₂·H₂O
M _r = 416.47
Monoclinic,
a = 11.3150 (2) Å
b = 17.4935 (3) Å
c = 10.5794 (2) Å
β = 94.731 (1)°
V = 2086.94 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.15 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.977, T _max = 0.981
18167 measured reflections
3768 independent reflections
2835 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.04
3768 reflections
305 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019525/sj2783sup1.cif

e-66-o1503-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019525/sj2783Isup2.hkl

e-66-o1503-Isup2.hkl^{(184.7KB, 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
N1—H5⋯O1ⁱ	0.87 (2)	2.05 (2)	2.9098 (19)	169.5 (18)
N2—H24⋯O2ⁱⁱ	0.862 (19)	2.16 (2)	2.9774 (19)	157.9 (16)
N3—H4⋯O3ⁱⁱ	0.93 (2)	1.87 (2)	2.787 (2)	168.1 (18)
O3—H1⋯O1ⁱⁱⁱ	0.94 (3)	1.88 (3)	2.747 (2)	152 (3)
O3—H2⋯O2	0.87 (3)	1.99 (3)	2.751 (2)	146 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank South China Normal University for financial support (grants SCNU033038 and SCNU524002).

supplementary crystallographic information

Comment

Pyrimidopyrimidine compounds have recently been paid much attention because of their therapeutic and pharmacological properties (Agarwal et al., 2005; Gangjee et al., 2005). As a part of our studies on the synthesis of the Biginelli-type compounds (Zhu et al., 2005), the title compound was synthesized by a one-pot three-component reaction between acetophenone, urea and benzaldehyde in presence of trimethylchlorosilane as a catalyst in a yield of 86% (Fig. 1) (Shi et al., 2007).

The bond lengths and angles in the molecule are normal (Allen et al., 1987). The asymmetric unit contains a pyrimidopyrimidine molecule and a solvate water molecule (Fig. 2). The organic molecule comprises two fused tetrahydropyrimidinone rings with phenyl substituents at the 4, and 5 positions on the tetrahydropyrimidinone rings and a third phenyl substituent at the ring junction 8 position. The 4- and 5- substituted phenyl rings are inclined at a dihedral angle of 22.72 (0.11) to one another and make angles of 47.95(0.07) and 65.76(0.07) with the third phenyl substituent.The molecules in the structure are linked via intermolecular N1—H5···O1 and N2—H24···O2 hydrogen bonds. In addition, the molecule is connected to the water molecule by N3—H4···O3, O3—H1···O1 and O3—H2···O2 hydrogen bonds which generate a three dimensional network (Fig. 3).

Experimental

Acetophenone (0.6 g, 5.0 mmol), urea (0.39 g, 6.5 mmol), benzaldehyde (0.53 g, 5.0 mmol), dimethyl sulfoxide (2.5 ml) and acetonitrile (5.0 ml) were mixed in a 25 ml flask and trimethylchlorosilane (0.54 g, 5.0 mmol) was added dropwise at room temperature (Fig. 1). Then the reaction mixture was stirred under 80°C for 5-6 h while a white precipitate was developing. The product was isolated by filtration through a Büchner funnel and washed first with water, then ethanol. The product was then dried to give a crystalline powder. Colourless, block-shaped single crystals of the title compound were obtained by slow evaporation from ethanol at room temperature.