N-bromobutanimide → ethyl 4-(bromomethyl)-2-(4-chloro-1-methyl-1H-pyrazol-5-yl)pyrimidine-5-carboxylate

HRID 339998Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:19])[C:6]=1[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][N:8]=1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:20][CH2:13][C:11]1[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][N:8]=[C:7]([C:6]2[N:5]([CH3:19])[N:4]=[CH:3][C:2]=2[Cl:1])[N:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-methylpyrimidine-5-carboxylate (1 g, 3.56 mmol) in carbon tetrachloride (20.0 mL) was added N-bromosuccinimide (697 mg, 3.92 mmol) and 2,2′-azo-bis-isobutyronitrile (30 mg, 0.2 mmol), and the reaction mixture was stirred at 80° C. overnight. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by combi-flash chromatography to afford 0.78 g (61% yield) of the desired product. LC-MS found: 361.1 (M+H)+.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customthe residue was purified by combi-flash chromatography

Sources & evidence

ORD record: ord-2d40804b3d1d41ef8ed6c0f0aea032a4
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895571B2

Reaction notes

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