Hydrochloric Acid → 1-[4-[4-(2-hydroxypropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea

Participants

Reaction Conditions

Reaction Steps

2-[2-Chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]propan-2-ol (160 mg, 0.59 mmol) was added to 3-(1,2-oxazol-3-yl)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea (242 mg) and Dichlorobis(triphenylphosphine) palladium catalyst (21 mg) in an 18% DMF in a mixture of 7:3:2 DME:water:ethanol (6 mL). The reaction was heated to 100° C. for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was acidified with 2M hydrochloric acid and the crude material loaded onto a SCX (10 g) column, the desired material was eluted with 7N ammonia in methanol. The material was further purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents, to give the desired material (52 mg) as a white solid.

Provenance & Evidence