Ammonia → Phenol, 4-[[2-amino-5-[(4-chlorophenyl)ethynyl]-4-pyrimidinyl]amino]-

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Reaction Steps

The brown solution was evaporated in vacuo (bath temperature 30° C.) to obtain a brownish-burgundy solid. The residue was stirred in dichloromethane and filtered to yield 0.4 g of 5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneamino-4-(4-hydroxyanilino)pyrimidine. The 1H NMR spectrum (CDCL3) was consistent with this structure. A mixture of 0.37 g of this product was heated in a bomb with 32 mL of methanolic ammonia at a temperature of 100° C. for five hours. The cooled bomb contents were evaporated in vacuo and triturated with ice cold water and dried to yield a mixture of the desired 2-amino-5-(4-chlorophenylethynyl)-4-(4-hydroxyanilino)pyrimidine with 2,4-diamino-5-(4-chlorophenylethynyl)pyrimidine.

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