2-Amino-6-hydroxymethylpyrimidine

2164-66-1

2164-67-2

General procedure for the synthesis of 2-amino-4-hydroxymethylpyrimidine from methyl 2-aminopyrimidine-4-carboxylate: 2-amino-4-methoxycarbonylpyrimidine (3.0 g, 20 mmol) was suspended in a solvent mixture of ethanol (150 mL) and dichloromethane (20 mL), followed by addition of sodium borohydride (2.2 g, 59 mmol). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, acetone (20 mL) was added slowly under cooling in an ice bath, followed by dropwise addition of 2M hydrochloric acid until no bubbles were produced. The pH of the reaction mixture was adjusted to 8 with saturated aqueous sodium bicarbonate and the precipitated solid was collected by filtration. The filtrate was concentrated under reduced pressure, suspended in 10% methanol-chloroform solution and filtered through silica gel (5.0 g). The filtrate was evaporated under reduced pressure and the residue was recrystallized from ethyl acetate to give 1.8 g of 2-amino-4-hydroxymethylpyrimidine as a light yellow solid (yield: 73%). The product was characterized by 1H-NMR (400 MHz, DMSO-d6): δ 4.30 (s, 2H), 5.35 (s, 1H), 6.48 (s, 2H), 6.65 (d, J = 4.9 Hz, 1H), 8.19 (d, J = 4.9 Hz, 1H).