N-bromobutanimide → Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(pyridin-3-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524724Notes

Reaction equation

HRID 524724 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])[NH:12][C:11]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[N:10]1.C1C(=O)N([Br:34])C(=O)C1>>[Br:34][CH2:20][C:13]1[NH:12][C:11]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH: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 118107537Ethyl 4-(2-chloro-4-fluorophenyl)-6-methyl-2-(pyridin-3-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107596Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(pyridin-3-yl)-1,4-dihydropyrimidine-5-carboxylateYield 70.1%

Procedure

Ethyl 4-(2-chloro-4-fluorophenyl)-6-methyl-2-(pyridin-3-yl)-1,4-dihydropyrimidine-5-carboxylate (5 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 (4.25 g, 70%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-5a1d3567a2a74b2f84470031f2a8e3f3
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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