2-(Methylthio)pyrimidine-5-carboxylic acid → 2-[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-(2-methylsulfanyl-pyrimidin-5-yl)-3-oxo-propionic acid ethyl ester

HRID 545346Notes

Reaction equation

HRID 545346 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([CH:20]1[CH2:22][CH2:21]1)[C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)[CH3:2].[CH3:24][S:25][C:26]1[N:31]=[CH:30][C:29]([C:32](O)=[O:33])=[CH:28][N:27]=1>>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([N:6]([CH:20]1[CH2:22][CH2:21]1)[C:7](=[O:19])[C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=1)[C:32]([C:29]1[CH:28]=[N:27][C:26]([S:25][CH3:24])=[N:31][CH:30]=1)=[O:33])[CH3:2]

Participants

3

Reactant 2

HCID 36317942-(Methylthio)pyrimidine-5-carboxylic acidHCID 67133328[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester2×

Product 1

HCID 671330872-[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-(2-methylsulfanyl-pyrimidin-5-yl)-3-oxo-propionic acid ethyl ester

Procedure

The title compound, a colorless oil (0.7 g, 32%), was prepared in analogy to intermediate 8A by reaction of [cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester (intermediate 7B) with 2-methylsulfanyl-pyrimidine-5-carboxylic acid (Arukwe, J.; Undheim, K. Acta Chem. Scand. Ser. B; 1986; 764-767). MS: 484.2 (MH+).

Sources & evidence

ORD record
ord-84de17536a81447fa73fd8d4c618ee0b
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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