N-Benzyl-4-methyl-6-phenyl­pyrimidin-2-amine

Hoong-Kun Fun; Madhukar Hemamalini; Anita Hazra; Shyamaprosad Goswami

doi:10.1107/S1600536811041365

. 2011 Oct 12;67(Pt 11):o2932. doi: 10.1107/S1600536811041365

N-Benzyl-4-methyl-6-phenylpyrimidin-2-amine

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Anita Hazra ^b, Shyamaprosad Goswami ^b

PMCID: PMC3247345 PMID: 22219963

Abstract

In the title compound, C₁₈H₁₇N₃, the dihedral angles between the central pyrimidine ring and its directly-bonded and N-bonded pendant phenyl rings are 25.48 (6) and 80.33 (6)°, respectively. The dihedral angle between the phenyl rings is 79.66 (6)°. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R ₂ ²(8) loops. The crystal structure also features weak π–π [centroid–centroid separation = 3.6720 (7) Å] and C—H⋯π interactions.

Related literature

For background to pyrimidine derivatives, see: Katrizky (1982 ▶); Brown & Lyall (1964 ▶). For a related structure, see: Goswami et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₇N₃
M _r = 275.35
Triclinic,
a = 8.2974 (1) Å
b = 9.9316 (2) Å
c = 10.7251 (2) Å
α = 115.797 (1)°
β = 93.019 (1)°
γ = 111.565 (1)°
V = 715.78 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.31 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.976, T _max = 0.985
14761 measured reflections
3272 independent reflections
2882 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.103
S = 1.08
3272 reflections
258 parameters
All H-atom parameters refined
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041365/hb6441sup1.cif

e-67-o2932-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041365/hb6441Isup2.hkl

e-67-o2932-Isup2.hkl^{(157.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041365/hb6441Isup3.cml

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

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

Cg1 is the centroid of the N1,N2/C7–C10 ring. Cg3 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N1ⁱ	0.909 (17)	2.147 (17)	3.0539 (14)	175.7 (14)
C5—H5A⋯Cg1ⁱⁱ	0.995 (14)	2.883 (15)	3.3595 (14)	110.3 (10)
C18—H18A⋯Cg3ⁱⁱⁱ	0.960 (16)	2.846 (19)	3.7977 (16)	171.8 (13)

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

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. SG and AH thank the CSIR [No. 01 (2292)/09/EMR-II], Government of India, for financial support.

supplementary crystallographic information

Comment

Substituted pyrimidine derivatives are important components of various bioactive molecules (Katrizky, 1982; Brown & Lyall, 1964). We have synthesised benzyl-(4-methyl-6-phenyl-pyrimidin-2-yl)-amine by solid-phase microwave irradiation (Goswami et al., 2009). Herein, we wish to report the crystal structure of the title compound, (I), (Fig. 1).

The central pyrimidine (N1,N2/C7–C10) ring makes dihedral angles of 25.48 (6) and 80.33 (6)° with the terminal phenyl (C1–C6/C12–C17) rings. The corresponding angle between the two terminal phenyl (C1–C6/C10–C15) rings is 79.66 (6)°.

In the crystal (Fig. 2), centrosymmetrically-related molecules are linked into dimers via pairs of N—H···N hydrogen bonds (Table 1), generating R₂²(8) ring motifs. (Bernstein et al., 1995). The crystal structure is further stabilized by π–π interactions between the benzene (Cg2; C1–C6) rings [Cg2···Cg2 = 3.6720 (7) Å; 1-x, -y, 1-z] and C—H···π interaction involving the centroids of the N1,N2/C7–C10 (Cg1) and C12–C17 (Cg3) rings.

Experimental

A mixture of S-methylisothiourea sulphate (556 mg, 2 mmol), potassium carbonate (345 mg, 2.5 mmol) and benzylamine ((428 mg, 4 mmol) was irradiated at 450 Watt for 18 minutes in a microwave oven. The solid mass was washed with chloroform to remove the unreacted benzylamine and then dried. The solid residue was then mixed with benzoyl acetone (648 mg, 4 mmol) and again irradiated at 300 Watt for 5 minutes. Water was added to it and the contents were extracted with chloroform. The crude product was then purified through column chromatography (silica gel, 100–200 mesh) using 12% ethyl acetate in petroleum ether as an eluent to afford the pure compound. Colourless blocks of (I) were grown by slow evaporation of a chloroform and methanol (3:1) solution. Mp 112–114°C.