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

HRID 524813Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:19])[NH:11][C:10]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[N:9]1.C1C(=O)N([Br:32])C(=O)C1>>[Br:32][CH2:19][C:12]1[NH:11][C:10]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[N:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 9841888Ethyl 4-(2-chlorophenyl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90043618Ethyl 6-(bromomethyl)-4-(2-chlorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 60%

Procedure

Ethyl 4-(2-chlorophenyl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (10 g, 27.6 mmol) was reacted with NBS (5.41 g, 30.4 mmol) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (7.3 g, 60%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-1a0ca87609e74e0cb8c27a77c9329c10
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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