Triethylamine → [(4S,5R)-4-(3-amino-phenyl)-5-ethyl-1,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

HRID 2409136Notes

Reaction equation

HRID 2409136 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[N:9]([CH3:27])[C:10](=[O:26])[C@H:11]([CH2:24][CH3:25])[C@@:12]([CH3:23])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)[N:13]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[N:9]([CH3:27])[C:10](=[O:26])[C@H:11]([CH2:24][CH3:25])[C@:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)([CH3:23])[N:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 57496603[(4S,5R)-5-ethyl-1,4-dimethyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 57496604[(4S,5R)-4-(3-amino-phenyl)-5-ethyl-1,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl esterYield 107.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of [(4S,5R)-5-ethyl-1,4-dimethyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (90 mg) in ethyl alcohol (2 ml), NEt3 (10 mg) and Pd/C (10%, 10 mg) was hydrogenated at normal pressure and 22° C. for 2 h. The mixture was filtered and the filtrate evaporated to give [(4S,5R)-4-(3-amino-phenyl)-5-ethyl-1,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (89 mg) as a colorless foam. MS (ESI): m/z=361.4 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-cc9d038acaf14592940f960275e5dd85
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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