[(S)-1-benzyl-4-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester → [(S)-4-(3-amino-phenyl)-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

HRID 1255787Notes

Reaction equation

HRID 1255787 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[N:9](CC2C=CC=CC=2)[C:10](=[O:24])[CH2:11][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].C(OC(=O)NC1N(CC2C=CC=CC=2)C(=O)C[C@](C2C=CC=C(N)C=2)(C)N=1)(C)(C)C>C(OCC)(=O)C.CO>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[NH:9][C:10](=[O:24])[CH2:11][C@:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)([CH3:23])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 57496578[(S)-1-benzyl-4-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl esterHCID 57501010[(S)-4-(3-amino-phenyl)-1-benzyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 66644141[(S)-4-(3-amino-phenyl)-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl esterYield 15.7%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Starting from [(S)-1-benzyl-4-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (0.98 mmole), the crude material was chromatographed on silica using n-heptane/ethyl acetate (5:2) to give a first fraction containing [(S)-4-(3-amino-phenyl)-1-benzyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (224 mg) as a colourless foam. MS (ESI): m/z=409.4 [ M+H]+ The second fraction was obtained using ethyl acetate/MeOH (9:1) to give [(S)-4-(3-amino-phenyl)-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (49 mg) as a colourless oil. MS (ESI): m/z=319.3 [ M+H]+.

Workup

  1. customthe crude material was chromatographed on silica
  2. customto give a first fraction
  3. customMS (ESI): m/z=409.4 [ M+H]+ The second fraction was obtained

Sources & evidence

ORD record
ord-99174738e65b46118a1c31b93c0af92f
Source dataset
uspto-grants-2013_06
Patent number
US08461160B2

Reaction notes

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