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

HRID 524699Notes

Reaction equation

HRID 524699 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[NH:12][C:11](Cl)=[N:10]1.[NH:22]1[CH:26]=[N:25][C:24]([C:27]#[N:28])=[N:23]1>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[NH:12][C:11]([N:22]2[CH:26]=[N:25][C:24]([C:27]#[N:28])=[N:23]2)=[N:10]1

Participants

3

Reactant 2

HCID 118107507Ethyl 4-(2-bromo-4-fluorophenyl)-2-chloro-6-methyl-1,4-dihydropyrimidine-5-carboxylateHCID 178510603HCID 178510603, compound

Product 1

HCID 90043467Ethyl 4-(2-bromo-4-fluorophenyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylateYield 50%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-2-chloro-6-methyl-1,4-dihydropyrimidine-5-carboxylate (3.77 g, 10 mmol) was reacted with 1H-1,2,4-triazole-3-carbonitrile (2.82 g, 30 mmol) according to the procedure as described in Example 48, Step A to give the title compound as a pale yellow solid (2.16 g, 50%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-fb5972eb99db426095fa0e63a916b7c8
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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