N-bromobutanimide → Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524704Notes

Reaction equation

HRID 524704 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]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)=[N:10]1.C1C(=O)N([Br:33])C(=O)C1>>[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]([CH2:20][Br:33])[NH:12][C:11]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)=[N:10]1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 118107539Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90042258Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylateYield 70%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylate (1.23 g, 3 mmol) was reacted with NBS (0.54 g, 3 mmol) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (1.02 g, 70%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-7e5c405d697043ea821ba613bcdc322e
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

Loading…