Ethyl Acetoacetate → Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1-methyl-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524693Notes

Reaction equation

HRID 524693 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[N:6][C:5]([C:8](=[NH:10])[NH2:9])=[N:4]1.[Br:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O.O=[C:22]([CH3:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[Br:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]1[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:22]([CH3:29])[NH:9][C:8]([C:5]2[N:6]=[CH:7][N:3]([CH3:2])[N:4]=2)=[N:10]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 900441211-methyl-1H-1,2,4-triazole-3-carboximidamide hydrochloride

Product 1

HCID 90043496Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1-methyl-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylateYield 63%

Procedure

1-methyl-1H-1,2,4-triazole-3-carboximidamide hydrochloride (3.3 g, 20 mmol) was reacted with 2-bromo-4-fluorobenzaldehyde (4 g, 20 mmol) and ethyl 3-oxobutanoate (2.6 g, 20 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a white solid (5.3 g, 63%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-2a8c46fa0ac744f2ab0f3ee1164b45a4
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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