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

HRID 524805Notes

Reaction equation

HRID 524805 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[S:22][C:23]([O:26][CH3:27])=[CH:24][N:25]=2)=[N:10]1.C1C(=O)N([Br:35])C(=O)C1>C(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]([C:21]2[S:22][C:23]([O:26][CH3:27])=[CH:24][N:25]=2)=[N:10]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90042921Ethyl 4-(2-bromo-4-fluorophenyl)-2-(5-methoxythiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90043009Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(5-methoxy thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-2-(5-methoxythiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate (2 g, 4.4 mmol) was reacted with NBS (0.78 g, 4.4 mmol) in DCM (50 mL) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (0.80 g, 34%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-381fed4a72e9496a885fe92997626370
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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