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

HRID 524804Notes

Reaction equation

HRID 524804 reaction equation
Cl.[CH3:2][O:3][C:4]1[S:8][C:7]([C:9](=[NH:11])[NH2:10])=[N:6][CH:5]=1.[Br:12][C:13]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=1[CH:15]=O.O=[C:23]([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>>[Br:12][C:13]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=1[CH:15]1[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([CH3:30])[NH:10][C:9]([C:7]2[S:8][C:4]([O:3][CH3:2])=[CH:5][N:6]=2)=[N:11]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 900443915-Methoxythiazole-2-carboximidamide hydrochloride

Product 1

HCID 90042921Ethyl 4-(2-bromo-4-fluorophenyl)-2-(5-methoxythiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylateYield 59%

Procedure

5-methoxythiazole-2-carboximidamide hydrochloride (3.3 g, 17 mmol) was reacted with 2-bromo-4-fluorobenzaldehyde (3.46 g, 17 mmol) and ethyl 3-oxobutanoate (2.2 g, 17 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (4.56 g, 59%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-a2d81939c6d749d5b43453a6b057ad33
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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