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

HRID 2409123Notes

Reaction equation

HRID 2409123 reaction equation
CO[C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[C@:5]([NH2:15])([C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:8]=1[F:14])[CH3:6].[CH3:19][NH:20][C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=S>>[C:26]([O:25][C:24](=[O:30])[NH:23][C:21]1[N:20]([CH3:19])[C:3](=[O:18])[C:4]([CH3:16])([CH3:17])[C@:5]([C:7]2[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:8]=2[F:14])([CH3:6])[N:15]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 57496573tert-butyl N-(methylcarbamothioyl)carbamateHCID 57497146HCID 57497146, compound

Product 1

HCID 57497154[(S)-4-(5-bromo-2-fluoro-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-(5-bromo-2-fluoro-phenyl)-2,2-dimethyl-butyric acid methyl ester and tert-butyl [(methylamino)carbonothioyl]carbamate, the product [(S)-4-(5-bromo-2-fluoro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester was obtained as a white solid. MS (ESI): m/z=442.2 and 444.1 [M+H]+.

Sources & evidence

ORD record
ord-5e064e5e38474e5688081d59784c8eb8
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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