1,1′,3,3′,5,5′-Hexamethyl­spiro­[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-penta­one

Nader Noroozi Pesyan; Saeed Rastgar; Yaser Hosseini

doi:10.1107/S1600536809019618

. 2009 May 29;65(Pt 6):o1444. doi: 10.1107/S1600536809019618

1,1′,3,3′,5,5′-Hexamethylspiro[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-pentaone

Nader Noroozi Pesyan ^a,^*, Saeed Rastgar ^a, Yaser Hosseini ^a

PMCID: PMC2969643 PMID: 21583282

Abstract

In the title molecule, C₁₅H₁₈N₄O₆, the fused 2,3-dihydrofuran ring has an envelope conformation and the spiro pyrimidine ring has a half-chair conformation. In the crystal, short intermolecular O⋯C contacts of 2.835 (4) and 2.868 (4) Å between the carbonyl groups indicate the existence of electrostatic interactions, which link the molecules into corrugated sheets parallel to the ab plane.

Related literature

For applications of furo[2,3-d]pyrimidine derivatives, see Cody et al. (1997 ▶). For a related crystal structure, see Malathy Sony et al. (2002 ▶).

Experimental

Crystal data

C₁₅H₁₈N₄O₆
M _r = 350.33
Orthorhombic,
a = 8.0122 (9) Å
b = 11.9181 (14) Å
c = 16.4037 (19) Å
V = 1566.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 120 K
0.21 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T _min = 0.980, T _max = 0.989
15042 measured reflections
1964 independent reflections
1589 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.089
S = 1.01
1964 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019618/cv2553sup1.cif

e-65-o1444-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019618/cv2553Isup2.hkl

e-65-o1444-Isup2.hkl^{(96.7KB, hkl)}

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

Table 1. Selected interatomic distances (Å).

C8⋯O2ⁱ	2.835 (4)
C3⋯O5ⁱⁱ	2.868 (4)

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

Acknowledgments

This work was supported by the Urmia University Research Council. We also thank Professor M. Yu. Antipin and Dr Z. Starikova for the X-ray data collection at the X-ray Structural Centre (XRSC), Moscow, Russia.

supplementary crystallographic information

Comment

Fused pyrimidine compounds are valued in view of their well-known biological properties. As example, the furo[2,3-d]pyrimidine antifolate derivative introduced as novel classical antitumor agent (Cody et al., 1997). Herewith we present the title compound, (I).

In (I) (Fig. 1),the fused 2,3-dihydrofuran ring has an envelope conformation, and spiro pyrimidine ring has a half-chair conformation. Spiro pyrimidine ring is nearly perpendicular to 2,3-dihydro furan ring moiety, as was observed earlier in the related compound (Malathy Sony et al., 2002). Torsion angles C2–C1–O4–C7 and C2–C1–C5–C6 are -99.39 (3)° and 94.87 (3)°, respectively. In the crystal, short intermolecular O···C contacts (Table 1) between the carbonyl groups prove an existing of electrostatic interactions, which link the molecules into corrugated sheets parallel to ab plane.

Experimental

In a 50 ml round bottom flask (in an ice-bath) equipped with magnetic stirrer was added 200 mg (1.89 mmol) cyanogen bromide in 10 ml acetone. Then a solution of 295 mg (1.89 mmol) 1,3-dimethylbarbituric acid and 202 mg (2.00 mmol) triethylamine in acetone was added drop wise by reparatory funnel during 1 h. The white solid precipitated after few minutes and the color of liquid turned red. Initially, the precipitate was dissolved in acetone. A white crystalline colorless solid was formed after allowing the solution to stand overnight (228 mg, 50% yield) as a white crystalline solid, m.p. 210–212 °C (decomps.); FT—IR (KBr), ν, cm^-1: 2981.54, 2954.71, 1689.08, 1646.35; ¹H NMR(CDCl₃, 300 MHz) δ 3.434 (s, 3H); 3.355 (s, 6H), 3.283 (s, 3H), 1.402 (s,6H); ¹³C NMR (CDCl₃, 75 MHz) δ 164.317, 160.207, 158.898, 151.033, 150.145, 93.220, 91.139, 53.872, 29.625, 29.081, 27.852, 23.318.