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

HRID 524763Notes

Reaction equation

HRID 524763 reaction equation
C(O)(=O)C.[F:5][C:6]([F:16])([F:15])[C:7]1[N:8]=[C:9]([C:12](=[NH:14])[NH2:13])[S:10][CH:11]=1.[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH:20]=O.O=[C:28]([CH3:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH:20]1[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]([CH3:35])[NH:13][C:12]([C:9]2[S:10][CH:11]=[C:7]([C:6]([F:5])([F:15])[F:16])[N:8]=2)=[N:14]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 134042,4-DichlorobenzaldehydeHCID 90043370HCID 90043370, compound

Product 1

HCID 118107593Ethyl 4-(2,4-dichlorophenyl)-6-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 64%

Procedure

4-(trifluoromethyl)thiazole-2-carboximidamide acetate (0.38 g, 1.49 mmol) was reacted with 2,4-dichlorobenzaldehyde (0.26 g, 1.49 mmol) and ethyl 3-oxobutanoate (0.2 g, 1.49 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (0.44 g, 64%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-fe5adf0514474c6ab284373588ca0f35
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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