Hydrochloric Acid → HCID 59540752, compound

Participants

Reaction Steps

To a solution of 1-[2-(3-methoxymethoxy-5-pyrrolidin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (492 mg, 0.91 mmol) in CH2Cl2 (1.5 ml) was added a solution of 10% ethanolic hydrogen chloride (4 ml, dry). The flask was capped and stirred for 2.5 hours. The volatile material was stripped (rotovap). Ethyl acetate (25 ml) and aqueous 5% Na2CO3 (25 ml) was added and the 2 phase system vigorously stirred for 3 minutes. The material was partitioned and the organic phase collected and washed with brine (25 ml). The aqueous phases were back extracted with EtOAc (2×20 ml). The organics were combined, dried (MgSO4), filtered and stripped to provide a crude semi-solid. The material was purified by preparative TLC, eluting with 38% ethyl acetate in hexanes to afford 326 mg of 1-[2-(3-hydroxy-5-pyrrolidin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow-brown solid.

Provenance & Evidence