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

HRID 524750Notes

Reaction equation

HRID 524750 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:25][N:24]=[CH:23][N:22]=2)=[N:10]1.C1C(=O)N([Br:33])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:33])[NH:12][C:11]([C:21]2[S:25][N:24]=[CH:23][N:22]=2)=[N:10]1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 90042385Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1,2,4-thiadiazol-5-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107530Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1,2,4-thiadiazol-5-yl)-1,4-dihydropyrimidine-5-carboxylateYield 40%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1,2,4-thiadiazol-5-yl)-1,4-dihydropyrimidine-5-carboxylate (5.7 g, 13.4 mmol) was reacted with NBS (2.87 g, 16.1 mmol) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (2.7 g, 40%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-5306df4cdedf4fc0970077048c1797af
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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