N-bromobutanimide → Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-1-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524621Notes

Reaction equation

HRID 524621 reaction equation
[Cl: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])[N:12]([CH3:21])[C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[N:10]1.C1C(=O)N([Br:34])C(=O)C1>>[Br:34][CH2:20][C:13]1[N:12]([CH3:21])[C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[N:10][CH:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Cl:1])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 90042905Ethyl 4-(2-chloro-4-fluorophenyl)-1,6-dimethyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107629Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-1-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 40%

Procedure

Ethyl 4-(2-chloro-4-fluorophenyl)-1,6-dimethyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.4 g, 1.02 mmol) was reacted with NBS (0.2 g, 1.12 mmol) according to the procedure as described in Example 1, Step B to give the title compound as yellow oil (0.19 g, 40%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-b04219807dcc42b8a572012d01768f13
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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