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

HRID 524558Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.Cl.[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19](=[NH:21])[NH2:20].O=[C:23]([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C([O-])(=O)C.[Na+]>C(O)C>[CH3:30][C:23]1[NH:20][C:19]([C:15]2[S:14][CH:18]=[CH:17][N:16]=2)=[N:21][CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[C:2]([F:12])([F:11])[F:1])[C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(trifluoromethyl)benzaldehyde (8.7 g, 50 mmol), thiazole-2-carboximidamide hydrochloride (8.2 g, 50 mmol), ethyl 3-oxobutanoate (7.8 g, 60 mmol) and sodium acetate (5.33 g, 65 mmol) in ethanol (90 mL) was refluxed at 80° C. for 12 hours under N2. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1) to give the title compound as a yellow solid (12.62 g, 64%). The compound was characterized by the following spectroscopic data:

Workup

filtrationThe resulting mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1)

Sources & evidence

ORD record: ord-df91b0a36a344e038a9c96c6262a66d6
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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