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

HRID 524562Notes

Reaction equation

[CH3:1][C:2]1[NH:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[N:5][CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:3]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].C1C(=O)N([Br:34])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:34][CH2:1][C:2]1[NH:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[N:5][CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:3]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 6-methyl-4-(2-nitrophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (7.45 g, 20 mmol) in carbon tetrachloride (100 mL) was added NBS (3.74 g, 21 mmol) under N2 at 60° C. The mixture was stirred at 60° C. for 10 minutes, and cooled to 25° C. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1) to give the title compound as a yellow solid (6.32 g, 70%). The compound was characterized by the following spectroscopic data:

Workup

temperaturecooled to 25° C
filtrationThe resulting mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1)

Sources & evidence

ORD record: ord-0070270c56f54e51b7f8df32971ebab8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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