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

HRID 524729Notes

Reaction equation

HRID 524729 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[C:26]([F:27])=[CH:25][C:24]([F:28])=[CH:23][C:22]=2[F:29])=[N:10]1.C1C(=O)N([Br:37])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:37])[NH:12][C:11]([C:21]2[C:22]([F:29])=[CH:23][C:24]([F:28])=[CH:25][C:26]=2[F:27])=[N:10]1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 118107607Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(2,4,6-trifluorophenyl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107540Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(2,4,6-tri fluorophenyl)-1,4-dihydropyrimidine-5-carboxylateYield 55.6%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(2,4,6-trifluorophenyl)-1,4-dihydropyrimidine-5-carboxylate (6.31 g, 13.4 mmol) (The compound was synthesized according to the procedure as described in CN200610098646.3) was reacted with NBS (2.87 g, 16.1 mmol) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (4.1 g, 55%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-b6ae779ba5c44457a14a44b8178fea1f
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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