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

HRID 524646Notes

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][CH:23]=[C:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[N:25]=2)=[N:10]1.C1C(=O)N([Br:38])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:38])[NH:12][C:11]([C:21]2[S:22][CH:23]=[C:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[N:25]=2)=[N:10]1

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 90043962Ethyl 4-(2-bromo-4-fluorophenyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107623Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 70.4%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate (1 g, 2 mmol) was reacted with NBS (0.39 g, 2.2 mmol) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (0.81 g, 70%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-70c6631e2a384299b29374b3b97bcee5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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