Methyl 6-(4-chloro­phen­yl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octa­hydro­chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxyl­ate

J Kanchanadevi; G Anbalagan; G Sivakumar; M Bakthadoss; V Manivannan

doi:10.1107/S160053681102678X

. 2011 Jul 9;67(Pt 8):o1990. doi: 10.1107/S160053681102678X

Methyl 6-(4-chlorophenyl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octahydrochromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxylate

J Kanchanadevi ^a, G Anbalagan ^b, G Sivakumar ^c, M Bakthadoss ^c, V Manivannan ^d,^*

PMCID: PMC3213446 PMID: 22091025

Abstract

In the title compound, C₂₄H₂₁ClN₂O₆, the two fused six-membered pyran rings adopt half-chair conformations. The dihedral angle between the pyrimidine ring and the chlorophenyl ring is 51.55 (3)°. In the crystal, molecules are linked by pairs of weak intermolecular C—H⋯O hydrogen bonds, forming inversion dimers. A C—H⋯π interaction is also observed.

Related literature

For biological activity of pyrimidine derivatives, see: Alam et al. (2005 ▶); Kappe (2000 ▶); Condon et al. (1993 ▶); Rovnyak et al. (1995 ▶); Leite et al. (2006 ▶); Sriram et al. (2006 ▶). For related structures, see: Booysen et al. (2011 ▶); Noroozi Pesyan et al. (2009 ▶).

Experimental

Crystal data

C₂₄H₂₁ClN₂O₆
M _r = 468.88
Monoclinic,
a = 10.6177 (5) Å
b = 11.9973 (5) Å
c = 17.5532 (8) Å
β = 99.751 (2)°
V = 2203.69 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.924, T _max = 0.951
29343 measured reflections
7232 independent reflections
4518 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.158
S = 1.03
7232 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.60 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102678X/is2742sup1.cif

e-67-o1990-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102678X/is2742Isup2.hkl

e-67-o1990-Isup2.hkl^{(346.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102678X/is2742Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg4 is the centroid of the C1–C5/C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O3ⁱ	0.93	2.44	3.349 (2)	166
C19—H19⋯Cg4ⁱⁱ	0.93	2.84	3.720 (3)	158

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

supplementary crystallographic information

Comment

Pyrimidine derivatives are used in the areas of pesticide and pharmaceutical agents (Condon et al., 1993). In addition, pyrimidine-2(1H)-ones/thiones are calcium channel blocker compounds (Rovnyak et al., 1995). They also have other biological activities such as antibacterial, antifungal and antiviral (Kappe, 2000; Alam et al., 2005; Sriram et al., 2006; Leite et al., 2006).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Booysen et al., 2011; Noroozi Pesyan et al., 2009). The sum of bond angles around N1 and N2 [359.93 (15) and 358.92°, respectively] indicates the sp² hybridization state of atoms N1 and N2 in the molecule. The crystal packing is controlled by weak intermolecular C—H···O and C—H···π interactions (Table 1).

Experimental

A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(4-chlorophenyl)acrylate (0.330 g, 1 mmol) and N,N-dimethylbarbutric acid (0.156 g, 1 mmol) was placed in a round bottom flask and melted at 180 °C for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided the pure product methyl-6-(4-chlorophenyl)-2,4-dimethyl-1,3-dioxo- 1,2,3,4,6,6a,7,12octahydrochromeno[4',3',4,5]pyrano[2,3-d]pyrimidine- 6a-carboxylate, as colorless solid in 96% yield.