2-Fluoro-2-methylpropanoic acid → (S)-N-(3-(2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenyl)-2-fluoro-2-methylpropanamide

HRID 2409141Notes

Reaction equation

HRID 2409141 reaction equation
C(OC(=O)[NH:7][C:8]1[N:9]([CH3:26])[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[C@:12]([C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)(C)(C)C.[F:28][C:29]([CH3:34])([CH3:33])[C:30](O)=[O:31]>>[NH2:7][C:8]1[N:9]([CH3:26])[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[C@:12]([C:15]2[CH:20]=[C:19]([NH:21][C:30](=[O:31])[C:29]([F:28])([CH3:34])[CH3:33])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1

Participants

3

Reactant 2

HCID 27828282-Fluoro-2-methylpropanoic acidHCID 57496584[(S)-4-(5-amino-2-fluoro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester2×

Product 1

HCID 66727504(S)-N-(3-(2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenyl)-2-fluoro-2-methylpropanamide

Procedure

The coupling of [(S)-4-(5-amino-2-fluoro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (intermediate F2) and 2-fluoro-2-methyl-propionic acid followed by deprotection of the intermediate yielded the title compound as a colorless amorphous solid. MS (ESI): m/z=367.2 [M+H]+.

Sources & evidence

ORD record
ord-24cfcacdb1754b1c93cac634b5b0acb6
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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