Sodium Hydroxide → 2-Hydroxymethyl-4-(4-(N,N-dimethylaminosulfonyl)-1-piperazino)pyrimidine

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Reaction Steps

11.0 g (35 mmol) of 4-[4-(N,N-dimethylsulfamoyl)piperazino]-2-methyloxymethylpyrimidine (Example 1) are dissolved in 45 ml of dry methylene chloride. Between 0° C. and +5° C., 13.2 g (52.5 mmol) of boron tribromide dissolved in 25 ml of methylene chloride are slowly added dropwise under argon. The mixture is stirred for a further 1.5 h while cooling in ice and is hydrolyzed with cold 2 N sodium hydroxide solution. The organic phase is separated off, and the aqueous phase is extracted 3 times more with methylene chloride. The combined organic phases are washed with saturated ammonium chloride solution, water and saturated sodium chloride solution and dried over sodium sulfate and the solvent is removed in vacuo. Crystallization of the residue in butyl acetate results in 7.60 g of solid product of melting point 148°-149° C.

Provenance & Evidence