benzyl N-[6-[[4-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]phenyl]methylcarbamoyl]-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidin-3-yl]carbamate → tert-butyl N-[4-[[[(6S)-3-amino-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HRID 10956Notes

Reaction equation

HRID 10956 reaction equation
C(OC(=O)[NH:10][C:11]1[C:16](=[O:17])[N:15]2[CH:18]([C:21](=[O:40])[NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[NH:31])=[CH:26][CH:25]=3)[CH2:19][CH2:20][C:14]2=[N:13][CH:12]=1)C1C=CC=CC=1>CO.[Pd]>[C:36]([O:35][C:33](=[O:34])[NH:32][C:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:21]([C@H:18]2[N:15]3[C:16](=[O:17])[C:11]([NH2:10])=[CH:12][N:13]=[C:14]3[CH2:20][CH2:19]2)=[O:40])=[CH:25][CH:26]=1)=[NH:31])([CH3:39])([CH3:37])[CH3:38]

Participants

4

Reactant 1

HCID 145857201benzyl N-[6-[[4-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]phenyl]methylcarbamoyl]-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidin-3-yl]carbamate

Product 1

HCID 145857226tert-butyl N-[4-[[[(6S)-3-amino-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of intermediate 1i (74.8 mg, 0.134 mmol) in 3 mL MeOH, was added 80 mg 10% Pd/C. The mixture was evacuated and flushed with H2 (3×), then it was stirred under an atmosphere of H2 for 24 h. The mixture was filtered and concentrated to afford 48 mg (84%) of intermediate 1j. MS (ESI) 427.08 (M+H+).

Workup

  1. customThe mixture was evacuated
  2. customflushed with H2 (3×)
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0c8fff419c2447b49520742bc9dd3e53
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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