Sodium Carbonate → 2-Amino-4,6-dimethyl pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 4.00 g (37.0 mmol) of guanidine sulfate and 8.40 g (79.3 mmol) of sodium carbonate in 25 mL of water were added 6.00 mL (58.1 mmol) of 2,4-pentanedione. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was poured into 150 mL of water and then extracted with two 150-mL portions of dichloromethane. The combined organic phase was washed with 150 mL of brine, dried (MgSO4) and then concentrated under diminished pressure to afford the expected product as a colorless solid: yield 4.31 g (95%); mp 152-153° C.; silica gel TLC Rf 0.50 (9:1 dichloromethane-methanol); 1H NMR (CDCl3) δ 2.24 (s, 6H), 5.39 (br s, 2H) and 6.33 (s, 1H); 13C NMR (CDCl3) δ 23.7, 23.7, 110.5, 162.9, 162.9 and 167.7; mass spectrum (APCI), m/z 124.0869 (M+H)1 (C6H10N3 requires 124.0875).

Provenance & Evidence