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

HRID 524726

Reaction equation

HRID 524726 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8](=[NH:10])[NH2:9].[Cl: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]>>[Cl: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:3]2[CH:4]=[N:5][CH:6]=[CH:7][N:2]=2)=[N:10]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 470895Pyrazine-2-carboxamidine hydrochloride

Product 1

HCID 118107549Ethyl 4-(2-chloro-4-fluorophenyl)-6-methyl-2-(pyrazin-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 41%

Procedure

Pyrazine-2-carboximidamide hydrochloride (5 g, 31.5 mmol) was reacted with 2-chloro-4-fluorobenzaldehyde (5 g, 31.5 mmol) and ethyl 3-oxobutanoate (4.1 g, 31.5 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (4.84 g, 41%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-2df5724b920746949c2d5f84a29dc7d2
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Linked notes

Loading…