tert-butyl N-(methylcarbamothioyl)carbamate → [(S)-4-(2-fluoro-5-nitro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

HRID 1255786Notes

Reaction equation

HRID 1255786 reaction equation
CO[C:3](=[O:20])[C:4]([CH3:19])([CH3:18])[C@:5]([NH2:17])([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[F:16])[CH3:6].[CH3:21][NH:22][C:23]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=S>>[C:28]([O:27][C:26](=[O:32])[NH:25][C:23]1[N:22]([CH3:21])[C:3](=[O:20])[C:4]([CH3:18])([CH3:19])[C@:5]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[F:16])([CH3:6])[N:17]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 57496573tert-butyl N-(methylcarbamothioyl)carbamateHCID 57496580(S)-3-amino-3-(2-fluoro-5-nitro-phenyl)-2,2-dimethyl-butyric acid methyl ester

Product 1

HCID 57497149[(S)-4-(2-fluoro-5-nitro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

Procedure

Starting from (S)-3-amino-3-(2-fluoro-5-nitro-phenyl)-2,2-dimethyl-butyric acid methyl ester and tert-butyl [(methylamino)carbonothioyl]carbamate (1.8 mmole), the product [(S)-4-(2-fluoro-5-nitro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (31 mg) was obtained as pale yellow oil. MS (ESI): m/z=407.3 [M−H]−. A second fraction contained [(R)-4-(2-methoxy-5-nitro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (270 mg) as a white solid. MS (ESI): m/z=419.3 [ M−H]−.

Sources & evidence

ORD record
ord-a70c97ec371440e282ea78584a9d3722
Source dataset
uspto-grants-2013_06
Patent number
US08461160B2

Reaction notes

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