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

HRID 524694Notes

Reaction equation

HRID 524694 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]([C:21]2[N:25]=[CH:24][N:23]([CH3:26])[N:22]=2)=[N:10]1.C1C(=O)N([Br:34])C(=O)C1>C(Cl)(Cl)Cl>[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:34])[NH:12][C:11]([C:21]2[N:25]=[CH:24][N:23]([CH3:26])[N:22]=2)=[N:10]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90043496Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1-methyl-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90043165Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1-methyl-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1-methyl-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate (5 g, 12 mmol) was reacted with NBS (2.1 g, 12 mmol) in chloroform (150 mL) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (2.4 g, 40%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-5e6ebe5b60d04258ac5bb2befb466c61
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

Loading…