Ethyl Acetoacetate → Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(5-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524809Notes

Reaction equation

HRID 524809 reaction equation
Cl.[F:2][C:3]([F:13])([F:12])[C:4]1[S:8][C:7]([C:9](=[NH:11])[NH2:10])=[N:6][CH:5]=1.[Br:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.O=[C:25]([CH3:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>>[Br:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]1[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([CH3:32])[NH:10][C:9]([C:7]2[S:8][C:4]([C:3]([F:2])([F:12])[F:13])=[CH:5][N:6]=2)=[N:11]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 900421955-(Trifluoromethyl)thiazole-2-carboximidamide hydrochloride

Product 1

HCID 118107591Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(5-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 23%

Procedure

5-(trifluoromethyl)thiazole-2-carboximidamide hydrochloride (0.93 g, 4 mmol) was reacted with 2-bromo-4-fluorobenzaldehyde (0.81 g, 4 mmol) and ethyl 3-oxobutanoate (0.55 g, 4.2 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (0.45 g, 23%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-deb17ba9b5134c569b505d0233712a36
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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