Methylamine → HCID 131714288, compound

Participants

Reaction Steps

A mixture of 2.6 g (8.0 mmole) of 4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]benzoic acid, 4.3 g (26.4 mmole) of diethyl phosphorocyanidate and 3.7 ml (26.4 mmole) of triethyl amine in 500 ml of N,N-dimethylformamide (dried over 4 Å molecular sieves overnight) was stirred at room temperature for five hours. Gaseous monomethylamine was passed into the suspension for one hour. The suspension initially became a clear solution and then a precipitate formed. The solvent was removed under high vacuum (0.1 mm, dry ice-2-propanol trap). The gummy residue was dissolved in 200 ml of ice water and neutralized to pH 7 by adding saturated sodium carbonate solution. The solid was collected and recrystallized from N,N-dimethylformamide to afford 15 g of the product as an off-white solid, mp 305° C. (with decomposition).

Provenance & Evidence