Aluminium lithium hydride → HCID 57378748, compound

Participants

Reaction Steps

135.7 mg (0.247 mmol) 2-[4-(tert-Butoxycarbonylaminocyclobutyl)phenyl]-3-phenylpyrimido[1,2-b]indazole-7-carboxylic acid methyl ester, described in example 10, were dissolved in 5 mL tetrahydrofuran. After addition of 18.8 mg (0.5 mmol) lithium aluminium hydride at −78° C., the reaction mixture was stirred was four hours. After addition of another equivalent lithium aluminium hydride stirring was continued for three hours at ° C. Stirring was further continued over night at room temperature. Additional four equivalents lithium aluminium hydride were added and the reaction mixture was stirred for 24 hours at room temperature. 96 mg {1-[4-(7-Hydroxymethyl-3-phenylpyrimido[1,2-b]indazol-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butylester were stirred over night in 6 mL 4M hydrogen chloride in dioxane. The solvent was evaporated and the residue was treated with saturated sodium bicarbonate. After extraction with dichloromethane (trice) the combined organic phases were washed with brine, dried and filtrated. The solvent was evaporated and the residue was purified by HPLC yielding 2.3 mg of the title compound.

Provenance & Evidence