Ethyl Acetoacetate → Ethyl 4-(5-fluoro-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524632Notes

Reaction equation

HRID 524632 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[C:5]([CH:18]=O)=[CH:4][CH:3]=1.Cl.[S:21]1[CH:25]=[CH:24][N:23]=[C:22]1[C:26](=[NH:28])[NH2:27].O=[C:30]([CH3:37])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:18]2[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:30]([CH3:37])[NH:27][C:26]([C:22]3[S:21][CH:25]=[CH:24][N:23]=3)=[N:28]2)=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 186795841,3-Thiazole-2-carboximidamide hydrochlorideHCID 1132420195-Fluoro-4'-(trifluoromethyl)biphenyl-2-carbaldehyde

Product 1

HCID 118107514Ethyl 4-(5-fluoro-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 32%

Procedure

5-fluoro-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carbaldehyde (2.11 g, 7.87 mmol) was reacted with thiazole-2-carboximidamide hydrochloride (1.29 g, 7.87 mmol) and ethyl 3-oxobutanoate (1.23 g, 9.44 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (1.22 g, 32%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-46f1e9c36c164a8a82173a5677af35b4
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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