4-Methyl-2,6-bis(pyrrolidin-1-yl)pyrimidine

In the crystal of the title compound, C13H20N4, the molecule is nearly planar, the dihedral angles between the pyrimidine and the two pyrrolidine rings being 4.71 (2) and 4.50 (2)°. The crystal features inversion-related dimers linked by pairs of C—H⋯N hydrogen bonds generating R 2 2(16) patterns. The dimeric units are further linked into C(6) chains via an additional C—H⋯N hydrogen bond.

In the crystal of the title compound, C 13 H 20 N 4 , the molecule is nearly planar, the dihedral angles between the pyrimidine and the two pyrrolidine rings being 4.71 (2) and 4.50 (2) . The crystal features inversion-related dimers linked by pairs of C-HÁ Á ÁN hydrogen bonds generating R 2 2 (16) patterns. The dimeric units are further linked into C(6) chains via an additional C-HÁ Á ÁN hydrogen bond.
The compound crystallizes in triclinic P-1 space group. In the crystal structure, the molecule is nearly planar, with the dihedral angles between the pyrimidine and the two pyrrolidine rings being 4.71 (2) and 4.50 (2)°. Further, the dihedral angle between the two pyrrolidine rings is 18.70 (2)°. The crystal structure features inversion-related dimers linked by pairs of C-H···N hydrogen bonds generating R 2 2 (16) patterns (Etter, 1990;Bernstein et al., 1995). The dimeric units are further linked into C(6) chains via an additional C-H···N hydrogen bond.
Experimental 2,4-Dichloro-6-methyl pyrimidine (3.11 mmol), pyrrolidine (6.83 mmol), and triethylamine (12.4 mmol) and 5 ml acetonitrile were taken in a microwave seal tube. The reaction mixture was irradiated with microwave for 90 min. The reaction was monitored by TLC with 30% ethyl acetate in petroleum ether. The solvent was removed and the residue dissolved in dichloromethane, purified by column chromatography, and the collected fraction was concentrated under reduced pressure. Single crystals employed in X-ray diffraction studies were obtained from slow evaporation of the solvent from the solution of the compound in ethyl acetate-petroleum ether at room temperature.

Refinement
The H atoms were positioned with idealized geometry using a riding model with C-H = 0.93 -0.97 Å. The isotropic displacement parameters for all H atoms were set to 1.2 times of the U eq of the parent atom (1.5 times of the U eq of the parent atom for CH 3 ).

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq N1 0.1352 (