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

HRID 524749Notes

Reaction equation

Cl.[S:2]1[C:6]([C:7](=[NH:9])[NH2:8])=[N:5][CH:4]=[N:3]1.[Br:10][C:11]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:12]=1[CH:13]=O.O=[C:21]([CH3:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[Br:10][C:11]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:12]=1[CH:13]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:21]([CH3:28])[NH:8][C:7]([C:6]2[S:2][N:3]=[CH:4][N:5]=2)=[N:9]1

Participants

Reactant 3

HCID 8868Ethyl Acetoacetate

HCID 27733192-Bromo-4-fluorobenzaldehyde

HCID 900431421,2,4-Thiadiazole-5-carboximidamide hydrochloride

Product 1

HCID 90042385Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1,2,4-thiadiazol-5-yl)-1,4-dihydropyrimidine-5-carboxylateYield 35.2%

Procedure

1,2,4-thiadiazole-5-carboximidamide hydrochloride (1.43 g, 8.69 mmol) was reacted with 2-bromo-4-fluorobenzaldehyde (1.76 g, 8.69 mmol) and ethyl 3-oxobutanoate (1.36 g, 10.5 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (1.3 g, 35%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-e0b50f0e30d04e6d84de5dfb534ffdf7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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