N-bromobutanimide → Ethyl 6-(bromomethyl)-4-(2,4-dichlorophenyl)-2-(4-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524764Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl: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[S:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=2)=[N:10]1.C1C(=O)N([Br:37])C(=O)C1>>[Br:37][CH2:20][C:13]1[NH:12][C:11]([C:21]2[S:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=2)=[N:10][CH:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 118107593Ethyl 4-(2,4-dichlorophenyl)-6-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90043072Ethyl 6-(bromomethyl)-4-(2,4-dichlorophenyl)-2-(4-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 70.5%

Procedure

Ethyl 4-(2,4-dichlorophenyl)-6-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.44 g, 0.94 mmol) was reacted with NBS (0.21 g, 0.94 mmol) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (0.36 g, 70%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-4bf0233e287046948588fc44166b22f5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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