N-Butyl-4,6-diphenyl­pyrimidin-2-amine

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

doi:10.1107/S160053681104147X

. 2011 Oct 12;67(Pt 11):o2956. doi: 10.1107/S160053681104147X

N-Butyl-4,6-diphenylpyrimidin-2-amine

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

PMCID: PMC3247364 PMID: 22219982

Abstract

In the title compound, C₂₀H₂₁N₃, the pyrimidine ring is inclined at dihedral angles of 51.57 (4) and 2.49 (4)° to the two phenyl rings. The dihedral angle between the two terminal phenyl rings is 50.44 (4)°. In the crystal, adjacent molecules are linked via a pair of N—H⋯N hydrogen bonds, forming an inversion dimer with an R ₂ ²(8) ring motif. Furthermore, the crystal structure is stabilized by a weak π–π interaction, with a centroid–centroid distance of 3.6065 (5) Å.

Related literature

For biological applications of pyrimidine derivatives, see: Katrizky et al. (1982 ▶); Brown & Lyall (1964 ▶). For the synthesis, 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

C₂₀H₂₁N₃
M _r = 303.40
Triclinic,
a = 8.1544 (1) Å
b = 9.5284 (1) Å
c = 11.3237 (2) Å
α = 77.090 (1)°
β = 74.152 (1)°
γ = 71.288 (1)°
V = 792.70 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.47 × 0.25 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.965, T _max = 0.993
26407 measured reflections
6933 independent reflections
5769 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.136
S = 1.04
6933 reflections
292 parameters
All H-atom parameters refined
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.31 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/S160053681104147X/is2788sup1.cif

e-67-o2956-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104147X/is2788Isup2.hkl

e-67-o2956-Isup2.hkl^{(332.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104147X/is2788Isup3.cml

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
N3—H1N3⋯N1ⁱ	0.869 (15)	2.262 (15)	3.1249 (10)	172.4 (15)

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Symmetry code: (i) Inline graphic .

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 utilized as antiviral and antifungal agents (Katrizky et al., 1982; Brown & Lyall, 1964). 2-Butylamino-4,6-diphenyl pyrimidine has been synthesized by solid-phase microwave irradiation (Goswami et al., 2009). The crystal structure of 2-butylamino-4,6-diphenylpyrimidine is reported here.

The molecular structure of the title compound is shown in Fig. 1. The pyrimidine (N1/N2/C7–C9/C16) ring is inclined at dihedral angles of 51.57 (4) and 2.49 (4)°, respectively, to the two phenyl (C1–C6 and C10–C15) rings. The corresponding angle between the two terminal phenyl (C1–C6 and C10–C15) rings is 50.44 (4)°.

In the crystal, (Fig. 2), the adjacent molecules are linked via a pair of N—H···N (Table 1) hydrogen bonds, forming an inversion dimer with an R₂²(8) ring motif (Bernstein et al., 1995). The crystal structure is further stabilized by a weak π–π interaction between the pyrimidine (Cg1; N1/N2/C7–C9/C16) and phenyl (Cg3; C10–C15) rings [Cg1···Cg3ⁱⁱ = 3.6065 (5) Å; (ii) 1 - x, 1 - y, -z].

Experimental

A mixture of S-methylisothiourea sulphate (556 mg, 2 mmol), potassium carbonate (345 mg, 2.5 mmol) and butylamine (292 mg, 4 mmol) was irradiated at 450 Watt for 12 minutes in a microwave oven. The solid mass was washed with chloroform to remove the unreacted butylamine and then dried. The solid residue was then mixed with dibenzoylmethane (896 mg, 4 mmol) and again irradiated at 300 Watt for 6 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 10% ethyl acetate in petroleum ether as an eluent to afford pure compound. The single crystal was grown by slow evaporation of a chloroform and methanol (3:1) solution (m.p. 65–66 °C).