Reaction #11056

Reaction equation

intermediate 1k

(6S)-[(4-{[(3-benzylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester

intermediate 1j

(S)-[(4-{[(3-amino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester

acetaldehyde

NaBH(OAc)3

→

intermediate 5a

Yield 60.5%

(S)-[(4-{[(3-ethylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester

Yield 60.5%

Conditions

Procedure

Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (101 mg, 0.24 mmol), acetaldehyde (21.1 mg, 0.48 mmol) and NaBH(OAc)3 (141.99 mg, 0.67 mmol) yielded 66 mg (60.5%) of intermediate 5a. MS (ESI) 455.1 (M+H+).

Source