Lithium Hydroxide → HCID 66909826, compound

Participants

Reaction Steps

2-(2-(2-(Bis(tert-butoxycarbonyl)amino)pyrimidin-5-yl)-6-morpholino-9H-purin-2-yl (400 mg) was reacted with methyl 3-bromopropionate via General Procedure C. The product, 468 mg of crude methyl 3-(2-(2-(bis(tert-butoxycarbonyl)amino)pyrimidin-5-yl)-6-morpholino-9H-purin-9-yl)propanoate, was reacted with 3 eq of lithium hydroxide in 1:1 THF/Water solution. After completion, the THF was removed under vacuum and the water solution was acidified to pH 2 using a concentrated HCl solution. The product precipitated as a white solid and was filtered to yield 388 mg 3-(2-(2-(tert butoxycarbonylamino)pyrimidin-5-yl)-6-morpholino-9H-purin-9-yl)propanoic acid of which 88 mg was subjected to Boc deprotection via General Procedure E to give 15.5 mg 114 as white solid following reverse phase purification. MS (Q1) 371.2 (M)+

Provenance & Evidence