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

HRID 524700Notes

Reaction equation

HRID 524700 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][C:23]([C:26]#[N:27])=[N:22]2)=[N:10]1.C1C(=O)N([Br:35])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:35])[NH:12][C:11]([N:21]2[CH:25]=[N:24][C:23]([C:26]#[N:27])=[N:22]2)=[N:10]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90043467Ethyl 4-(2-bromo-4-fluorophenyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90043056Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylateYield 80.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate (0.35 g, 0.8 mmol) was reacted with NBS (0.14 g, 0.81 mmol) in chloroform (15 mL) according to the procedure as described in Example 1, Step B to give the title compound as pale yellow oil (0.33 g, 80%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-7030f849beb743d68980b255361a4120
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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