N-Methyl-2-pyrimidinamine

Intermediate AT: l-methyl-5-phenyl-1H-imidazol-2-amineStep 1: Synthesis of N-methylpyrimidin-2-amineTo a solution of 2-chloropyrimidine (1 g, 8.7 mmol) in methanol (10 mL) is added a 2M solution of methylamine (13.2 mL, 26.2 mmol) in methanol, followed by KTo a solution of 2-aminopyrimidine (3.00 g, 31.55 mmol) in acetone (50 mL) iodomethane (6.87 mL, 110.41 mmol) was added and reaction mixture was stirred on the oil bath at 75 C overnight. After the reaction mixture was allowed to reach rt, the resulting white precipitate was filtered off, washed with acetone (2 × 30 mL), ether (2 × 30 mL) and dissolved in ethanol (60 mL). To this a 10% solution of sodium hydroxide in water (40 mL) was added and the reaction mixture was heated at 80 C for 0.5 h upon vigorous stirring. Then the reaction mixture was poured into ice and extracted by dichloromethane (3 × 30 mL). The combined organic phases were washed with water (30 mL), brine (3 × 20 mL), dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. Yield, 75% (2.59 g); colorless crystals; mp 55-59 C (60-62 C, lit [1]); IR (KBr) nu = 3260, 3114, 3045, 2951, 2903, 2859, 1578, 1538, 1461, 1389, 1363, 1272, 1219, 1176, 1151, 1103, 1070, 987, 832, 798, 780 cm-1. 1H NMR (CDCl3) delta 3.02 (d, 3H, 3J = 5.2 Hz, CH3), 5.25 (br s, 1H, NH), 6.54 (t, 1H, 3J = 4.8 Hz, Ar-H-5), 8.31 (d, 2H, 3J = 4.8 Hz, Ar-H-4, Ar-H-6); 13C NMR (DMSO-d6) delta 28.24 (CH3), 110.13, 158.30, 163.22; MS (ESI) m/z (%) = 110 (MH+, 100). HRMS for C5H8N3: calculated 110.0718; found 110.0713.

Molecular Weight:109.13
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:109.063997236
Monoisotopic Mass:109.063997236
Topological Polar Surface Area:37.8
Heavy Atom Count:8
Complexity:58.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes