Sulfuric Acid → HCID 178497740, compound

Participants

Reaction Steps

A mixture of 0.71 g (1.05 eq) of guanidine hydrochloride, 0.40 g (1.05 eq) of sodium methoxide, and 20 mL of anhydrous methanol is stirred under nitrogen for 30 minutes. The solid which forms is removed by filtration and the filtrate concentrated under reduced pressure. To the residue (guanidine free base) is added 2.15 g (1.0 eq) of methyl 4-(5-carbethoxy-5-cyanopentyl)benzoate in 20 mL of anhydrous dimethylformamide. This mixture is stirred under nitrogen with gentle heating for 12 hours, cooled, and then mixed with very dilute sulfuric acid. The solid is collected, washed with water and then diethyl ether, and dried to yield methyl 4-[4-(2,4-diamino-6-hydroxypyrimidin-5-yl)butyl]-benzoate, m.p. 203°-205° C.; IR (KBR) vmax 3495, 3380, 2925, 2850, 1685, 1600, 1490, 1430, 1359, 1282, 1174, 1111, 1015, and 754 cm-1 ; 1H NMR (d6DMSO) delta 9.74 (bs, 1H (3)--NH), 7.83 (d, J=8.1 Hz, 2H, Ar), 7.31 (d, J=8.1 Hz, 2H, Ar), 5.87 (bs, 2H (2)--NH2), 5.60 (bs, 2H, (6)--NH2), 3.80 (s, 3H, CH3), 2.62 (t, J=7.6 Hz, 2H, (5)--CH2), 2.15 (t, J=7.2 Hz, 2H, benzyl), 1.51-1.55 (m, 2H, 2° aliphatic), 1.26-1.28 (m, 2H 2° aliphatic).

Provenance & Evidence