Ethyl Acetoacetate → Ethyl 4-(2-chloro-4-fluorophenyl)-6-methyl-2-(pyridin-3-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524723

Reaction equation

HRID 524723 reaction equation
Cl.[C:2](=[NH:10])([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[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:2]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[N:10]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 202042Nicotinamidine hydrochloride

Product 1

HCID 118107537Ethyl 4-(2-chloro-4-fluorophenyl)-6-methyl-2-(pyridin-3-yl)-1,4-dihydropyrimidine-5-carboxylateYield 50%

Procedure

Nicotinimidamide hydrochloride (4.97 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 (5.89 g, 50%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-e6c117d25ebb49a2b9605974687e4d75
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Linked notes

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