2-Chloro-6-methylaniline → HCID 22125119, compound

Participants

Reaction Steps

A mixture of 2.6 g (5 mmol) of 4-(3-(2-(tert-butyldiphenylsilyloxy)ethyl)phenylamino)-5-formyl-2-methylthiopyrimidine and 0.63 ml (722 mg, 5.1 mmol) of 2-chloro-6-methylaniline in 80 ml of toluene was treated with 170 mg (0.9 mmol) of 4-toluenesulfonic acid monohydrate and then heated at reflux with azeotropic removal of water for 2 hours. The mixture was cooled and evaporated. The residue was dissolved in 20 ml of tetrahydrofuran and added dropwise to a solution of 5 ml (5 mmol) of lithium aluminium hydride (1M solution in tetrahydrofuran) in a further 30 ml of tetrahydrofuran. After stirring for 1 hour the reaction was quenched by the cautious dropwise addition of 1.5 ml of water, 2 ml of 2M aqueous sodium hydroxide and 2.5 ml of water. The mixture was filtered through a filter aid and the filtrate evaporated to give 3.3 g (100%) of 4-[3-(2-(tert-butyldiphenylsilyloxy)ethyl)phenyl]amino-5-(2-chloro-6-methylanilino)methyl-2-methylthiopyrimidine as a yellow oil which was used without further purification. [Mass spectrum (ESI) MH+ =653].

Provenance & Evidence