Ethyl 4-(4-hydroxy­phen­yl)-6-methyl-2-thioxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate monohydrate

Bo Liu; Mingjie Zhang; Naijing Cui; Jie Zhu; Jin Cui

doi:10.1107/S1600536807065737

. 2007 Dec 12;64(Pt 1):o261. doi: 10.1107/S1600536807065737

Ethyl 4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monohydrate

Bo Liu ^a, Mingjie Zhang ^a,^*, Naijing Cui ^a, Jie Zhu ^a, Jin Cui ^a

PMCID: PMC2915317 PMID: 21200826

Abstract

In the organic molecule of the title compound, C₁₄H₁₆N₂O₃S·H₂O, the two rings are oriented at a dihedral angle of 84.31 (2)°. In the crystal structure, intramolecular O—H⋯O and intermolecular O—H⋯O, N—H⋯O, O—H⋯S and N—H⋯S hydrogen bonds are found.

Related literature

For general background, see: Atwal et al. (1991 ▶); Mayer et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₆N₂O₃S·H₂O
M _r = 310.36
Triclinic,
a = 5.6702 (17) Å
b = 11.212 (3) Å
c = 12.343 (4) Å
α = 90.406 (5)°
β = 95.251 (5)°
γ = 104.393 (5)°
V = 756.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 294 (2) K
0.22 × 0.16 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.951, T _max = 0.964
3958 measured reflections
2655 independent reflections
1741 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.117
S = 1.01
2655 reflections
209 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065737/hk2363sup1.cif

e-64-0o261-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065737/hk2363Isup2.hkl

e-64-0o261-Isup2.hkl^{(130.4KB, 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
O4—H4B⋯O1ⁱ	0.855 (10)	1.999 (14)	2.835 (3)	166 (3)
O4—H4A⋯S1ⁱⁱ	0.87 (3)	2.44 (2)	3.189 (2)	145 (3)
N2—H2A⋯O3ⁱⁱⁱ	0.892 (10)	2.097 (11)	2.988 (3)	177 (3)
N1—H1A⋯S1^iv	0.895 (10)	2.479 (11)	3.363 (2)	170 (2)
O3—H3⋯O4	0.82	1.90	2.724 (3)	179

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

supplementary crystallographic information

Comment

The title compound, (I), is a kind of polyfunctionalized dihydropyrimidines (DHPMs), which represents a heterocyclic system of remarkable pharmacological efficiency and may exhibit antiviral, antitumor, antibacterial, and anti inflammatory properties (Atwal et al., 1991). It is the only cell-permeable molecule currently known to specifically inhibit mitotic kinesis Eg5 and is considered a lead for the development of new anticancer drugs (Mayer et al., 1999).

In the molecule of the title compound, (I), (Fig.1) the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (N1/N2/C1—C4) and B (C9—C14) are, of course, planar and they are oriented at a dihedral angle of A/B = 84.31 (2)°.

In the crystal structure, intramolecular O—H···O and intermolecular O—H···O, N—H···O, O—H···S and N—H···S hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, a solution of ethyl acetoacetate (1.44 g, 10 mmol), 4-hydroxybenzaldehyde (1.38 g, 10 mmol) and thiourea (0.86 g, 10 mmol) in ethanol (5 ml) was heated under reflux in the presence of HCl (three drops) for 2.5 h. After being cooled to room temperature, the reaction mixture was poured onto crushed ice (30 g) and stirred for 5–10 min. The separated solid was filtered under suction (water aspirator), washed with ice-cold water (50 ml), and then recrystallized from hot ethanol to afford the pure product.