{1-[6-(3,4-Difluoro-phenoxy)-4-pyrimidin-2-yl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester → 2-Amino-1-[6-(3,4-difluoro-phenoxy)-4-pyrimidin-2-yl-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-one

HRID 1965175Notes

Reaction equation

HRID 1965175 reaction equation
C(OC(=O)[NH:10][CH:11]([C:16]([N:18]1[CH2:22][CH2:21][CH:20]2[N:23]([C:35]3[N:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH2:24][CH:25]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[CH:19]12)=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13])C1C=CC=CC=1>CO>[NH2:10][CH:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:16]([N:18]1[CH2:22][CH2:21][CH:20]2[N:23]([C:35]3[N:36]=[CH:37][CH:38]=[CH:39][N:40]=3)[CH2:24][CH:25]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[CH:19]12)=[O:17]

Participants

3

Reactant 1

HCID 67608380{1-[6-(3,4-Difluoro-phenoxy)-4-pyrimidin-2-yl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester

Product 1

HCID 675059372-Amino-1-[6-(3,4-difluoro-phenoxy)-4-pyrimidin-2-yl-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of carbamate 29 (140 mg, 0.25 mmol) and 10% Pd-on-carbon (wet, 100 mg, 0.09 mmol) in MeOH (20 mL) was stirred vigorously under 1 atm H2. After 3 h, the catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe filter and the solvent was removed in vacuo to afford 106 mg (100%) of 30 as a white solid which was used without further purification. Mass spectrum, m/z [431.8] (M+H)+.

Workup

  1. customthe catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe
  2. filtrationfilter
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3fe3814ecb2141f89a8b51d3161263f4
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

Loading…