Phosphorus oxychloride → 6-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N-isopropylpyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round-bottomed flask was placed 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(isopropylamino)pyrimidin-2-ol (29, 124 mg, 0.469 mmol) in POCl3 (20 ml) to give a yellow solution. The mixture was stirred at 100° C. for 16 h. The mixture was cooled to room temperature, concentrated, diluted with dichloromethane and washed with saturated NaHCO3 followed by 0.2 N NaOH. The organic phase was dried over MgSO4, filtered and concentrated to give the title compound (91 mg, 69%). Aryl chloride 30 could be transformed into aniline 18 as described in scheme 2 for the conversion of 5 into 6. Aniline 18 could be transformed into urea or carbamate compounds as described in scheme 2 (and illustrated in the experimental section for scheme 7).

Provenance & Evidence