3-(4-Fluoro­phen­yl)-2-(2-naphth­yloxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

Jun-Kai Ma; Mei He; Yang-Gen Hu

doi:10.1107/S1600536809039531

. 2009 Oct 3;65(Pt 11):o2629. doi: 10.1107/S1600536809039531

3-(4-Fluorophenyl)-2-(2-naphthyloxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

Jun-Kai Ma ^a, Mei He ^b, Yang-Gen Hu ^c,^*

PMCID: PMC2970989 PMID: 21578245

Abstract

The title compound, C₂₉H₁₇FN₄O₂, may be used as a new precursor for obtaining bioactive molecules. There are two crystallographically independent molecules in the asymmetric unit. The phenyl ring, 4-fluorophenyl ring and 2-naphthyloxy ring are twisted with respect to the pyrrolopyrimidine ring by 52.30 (11)/49.05 (11), 80.94 (10)/88.36 (10) and 60.58 (7)/83.76 (7)°, respectively. The crystal packing is stabilized by weak C—H⋯N hydrogen bonds.

Related literature

For the biological activity of pyrimidinone derivatives, see: Kondo et al. (1986 ▶) and for their pharmaceutical activity, see: Bayomi et al. (1986 ▶); Ding et al. (2004 ▶). For related structures, see: He et al. (2007 ▶); Hu et al. (2005 ▶, 2006 ▶, 2007 ▶).

Experimental

Crystal data

C₂₉H₁₇FN₄O₂
M _r = 472.47
Triclinic,
a = 9.8522 (16) Å
b = 14.549 (2) Å
c = 16.792 (3) Å
α = 101.755 (3)°
β = 90.840 (3)°
γ = 103.789 (3)°
V = 2283.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.985, T _max = 0.991
14836 measured reflections
8839 independent reflections
5302 reflections with I > 2σ(I)
R _int = 0.082

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.129
S = 0.93
8839 reflections
649 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 datablocks I, global. DOI: 10.1107/S1600536809039531/bt5077sup1.cif

e-65-o2629-sup1.cif^{(36.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039531/bt5077Isup2.hkl

e-65-o2629-Isup2.hkl^{(432.3KB, 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
C45—H45⋯N4ⁱ	0.93	2.48	3.312 (3)	150
C15—H15⋯N8ⁱⁱ	0.93	2.48	3.294 (3)	147

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

Acknowledgments

We gratefully acknowledge financial support of this work by the Key Science Research Project of the Hubei Provincial Department of Education (No. D200724001) and the Science Research Project of Yunyang Medical College (No. 2006QDJ16)

supplementary crystallographic information

Comment

Derivatives of pyrimidinone are attracting increasing attention in the synthetic chemistry community because of the important role played by such systems in many natural products, also in antibiotics and drugs (Kondo et al.,1986; Bayomi et al., 1986; Ding et al., 2004). Recently, aza-Wittig reaction of functionalized iminophosphoranes with isocyanates were applied to produce carbodiimides able to undergo a plethora of heterocyclization reactions (Hu et al., 2005, 2006, 2007 and He et al., 2007). As a part of our ongoing investigations on the preparation of the heterocyclic compounds, we have synthesized and structurally characterized the title compound. In the crystal structure of title compound two crystallographically independent molecules are found in the asymmetric unit. All ring atoms of pyrrolopyrimidine ring system are coplanar, with a maximum deviation of -0.024Å for atom C12. The phenyl ring and 4-fluorophenyl ring, 2-naphthalenyloxy ring are twisted with the pyrrolopyrimidine rings by 52.30 (11)/49.05 (11)°, 80.94 (10)/88.36 (10)°, 60.58 (7)/83.76 (7)°,respectively. The crystal packing is mainly stabilized by C—H···N (Table 1).

Experimental

The title compound was obtained in excellent yield via aza-Wittig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:2 v/v) at room temperature.