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

HRID 524645Notes

Reaction equation

HRID 524645 reaction equation
Cl.[C:2]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[N:9]=1)(=[NH:4])[NH2:3].[Br:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:17]=1[CH:18]=O.O=[C:26]([CH3:33])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[Br:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:17]=1[CH:18]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([CH3:33])[NH:3][C:2]([C:5]2[S:6][CH:7]=[C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[N:9]=2)=[N:4]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 90043737Methyl 2-(2-carbamimidoylthiazol-4-yl)acetate hydrochloride

Product 1

HCID 90043962Ethyl 4-(2-bromo-4-fluorophenyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylateYield 50%

Procedure

Methyl 2-(2-carbamimidoylthiazol-4-yl)acetate hydrochloride (2.35 g, 10 mmol) was reacted with 2-bromo-4-fluorobenzaldehyde (2.03 g, 10 mmol) and ethyl 3-oxobutanoate (1.56 g, 12 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (2.48 g, 50%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-7cfe3fa2a8e44e0887e61b52eb781c08
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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