Methanol → Benzenemethanol, 4-((2,4-diamino-5-pyrimidinyl)methyl)-2,6-dimethoxy-

Participants

Reaction Conditions

Reaction Steps

135 Ml. of about 15% diisobutylaluminum hydride solution in dioxane were added dropwise within 30 minutes at 50°C. under nitrogen and exclusion of moisture to a solution of 4.45 g. of α-(2,4-diamino-5-pyrimidinyl)-2,6-dimethoxy-p-toluic acid methyl ester in 400 ml. of absolute dioxane. The resulting suspension was stirred at 50° for 1 hour. After cooling to 30°C., the reaction mixture was treated with a mixture of 25 ml. of methanol, 5 ml. of water and 50 ml. of dioxane and stirred at 50° for an additional 2 hours. The solid material was separated and rejected, and the filtrate was evaporated to dryness. After recrystallization from about 20 ml. of methanol, the residue yielded 4-[ (2,4-diamino-5-pyrimidinyl)-methyl] -2,6-dimethoxybenzyl alcohol having a m.p. of 227°-228°.

Provenance & Evidence