Toluene → HCID 67047279, compound

Participants

Reaction Conditions

Reaction Steps

A 50 ml round bottom flask was charged with 0.09 g (0.14 mmol) of 3-(5-amino-4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-ylamino)pyrimidin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile (prepared from 3-(5-nitro-4-thiocyanatopyrimidin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile and (1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amine via same procedure as in Example H, step 1 and Example B, step 3). 20 ml of toluene was then added, followed by 0.028 g (0.21 mmol) of N,N-dimethylformamide dimethylacetal, and a catalytic amount of pyridinium p-toluenesulfonate. The resulting mixture was stirred at 100° C. overnight (condenser used with flask). The mixture was cooled to room temp, diluted with 100 ml EtOAc and washed with approx 10 ml water. The organic layer was dried over MgSO4 and concentrated in vacuo, and purified by column chromatography (eluting with 1% MeOH in DCM), to give 0.06 g (65%) of the titled compound. Compound was single peak by HPLC and had an M+H of 660 by MS.

Provenance & Evidence