N-bromobutanimide → 5-Bromo-6-chloro-2-(methylsulfanyl)pyrimidin-4-amine

HRID 63601Notes

Reaction equation

HRID 63601 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8]([CH3:10])=O)[N:5]=[C:4]([NH2:11])[CH:3]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)Cl>[Br:12][C:3]1[C:4]([NH2:11])=[N:5][C:6]([S:8][CH3:10])=[N:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15563630HCID 15563630, compound

Product 1

HCID 123694275-Bromo-6-chloro-2-(methylsulfanyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold stirring solution of 10 g (52.2 mmol) 6-chloro-2-(methylsulfinyl)pyrimidine-4-amine in 450 ml of DCM, 10 g (56.2 mmol) of N-bromosuccinimide were added, and stirring was continued for 1 hour at room temperature to provide 5-bromo-6-chloro-2-(methylthio)pyrimidine-4-amine, which was used without further purification in the next step (see intermediate 3). The end of the reaction is followed by thin layer chromatography.

Sources & evidence

ORD record
ord-b6e875bc27c641fda5fef35ae7d10504
Source dataset
uspto-grants-2016_09
Patent number
US09447095B2

Reaction notes

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