6-(2,6-Dimethyl­phen­yl)pyrido[2,3-d]pyrimidin-7-amine

Seiji Nukui; Arnold L Rheingold; Antonio DiPasquale; Alex Yanovsky

doi:10.1107/S1600536809006242

. 2009 Feb 25;65(Pt 3):o591. doi: 10.1107/S1600536809006242

6-(2,6-Dimethylphenyl)pyrido[2,3-d]pyrimidin-7-amine

Seiji Nukui ^a, Arnold L Rheingold ^b, Antonio DiPasquale ^b, Alex Yanovsky ^a,^*

PMCID: PMC2968671 PMID: 21582246

Abstract

In the title compound, C₁₅H₁₄N₄, the pyrido[2,3-d]pyrimidine system is almost ideally planar (r.m.s. deviation 0.028 Å) with its mean plane almost orthogonal to the 2,6-dimethylphenyl plane. The dihedral angle formed by these planes [87.3 (2)°] is close to the predicted value (89.7°) obtained by molecular-mechanics force-field calculations. Only one of the two active amine H atoms participates in hydrogen bonding, which links molecules into centrosymmetric dimers.

Related literature

For the structures of related pyrido[2,3-d]pyrimidine derivatives, see: Hamby et al. (1997 ▶); Trumpp-Kallmeyer et al. (1998 ▶). For the synthesis of the title compound, see: Bennett et al. (1981 ▶); Blankley & Bennett (1981 ▶). For molecular-mechanics force-field calculations, see: Duan et al. (2003 ▶).

Experimental

Crystal data

C₁₅H₁₄N₄
M _r = 250.30
Monoclinic,
a = 16.272 (3) Å
b = 10.644 (2) Å
c = 15.234 (3) Å
β = 109.118 (3)°
V = 2493.0 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 208 K
0.14 × 0.06 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.988, T _max = 0.995
6161 measured reflections
2863 independent reflections
1706 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.152
S = 0.98
2863 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-32 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006242/rz2295sup1.cif

e-65-0o591-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006242/rz2295Isup2.hkl

e-65-0o591-Isup2.hkl^{(140.6KB, 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
N4—H4A⋯N1ⁱ	0.87	2.18	3.044 (2)	171

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The present X-ray study confirmed the structure of the compound reported in Bennett et al. (1981) as 6-(2,6-dimethylphenyl)pyrido[2,3-d]pyrimidin-7-amine. The pyrido[2,3-d]pyrimidine system of the molecule of the title compound (Fig. 1) is planar within 0.045 Å. The 2,6-dimethylphenyl plane is approximately orthogonal to the mean plane of the bicyclic system; the corresponding dihedral angle [87.3 (2)°] is close to predicted value (89.7°), obtained by molecular mechanics force field calculations (Duan et al., 2003). The overall geometry of the molecule is quite close to the structures of previously studied phenyl substituted 7-aminopyrido[2,3-d]pyrimidines (Hamby et al., 1997; Trumpp-Kallmeyer et al., 1998).

Only one of the two amine H atoms (H4A) participates in the H-bonding (Table 1), which is responsible for formation of centrosymmetric dimers in the crystal. The H4B atom is close to the π-electron density of the phenyl ring and is not involved in either intra- or intermolecular H-bonding.

Experimental

The title compound was synthesized according to Bennett et al. (1981) and Blankley & Bennett (1981).