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

HRID 524717Notes

Reaction equation

HRID 524717 reaction equation
Cl.[F:2][C:3]1[C:4]([C:9](=[NH:11])[NH2:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[Cl: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]>>[Cl: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:4]2[C:3]([F:2])=[CH:8][CH:7]=[CH:6][N:5]=2)=[N:11]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 220278373-Fluoropicolinimidamide hydrochloride

Product 1

HCID 9930383Ethyl 4-(2-chloro-4-fluorophenyl)-2-(3-fluoropyridin-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylateYield 45.1%

Procedure

3-fluoropicolinimidamide hydrochloride (5.53 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 (5.56 g, 45%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-9cc77fad402049dbacfe7beaceb9de17
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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