m-Chloroperbenzoic acid → 5-Bromo-6-chloro-2-methanesulfinylpyrimidin-4-amine

HRID 63602

Reaction equation

HRID 63602 reaction equation
[Br:1][C:2]1[C:3]([NH2:11])=[N:4][C:5]([S:9][CH3:10])=[N:6][C:7]=1[Cl:8].ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Br:1][C:2]1[C:3]([NH2:11])=[N:4][C:5]([S:9]([CH3:10])=[O:20])=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 123694275-Bromo-6-chloro-2-(methylsulfanyl)pyrimidin-4-amine2×

Product 1

HCID 866770165-Bromo-6-chloro-2-methanesulfinylpyrimidin-4-amineYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 5-bromo-6-chloro-2-(methylthio)pyrimidine-4-amine (intermediate 1) (52.2 mmol) in 450 ml of DCM, a solution of 12.9 g (57.4 mmol) of m-chloroperbenzoic acid (77%) (Sigma-Aldrich) in 100 ml of DCM was slowly added. The reaction mixture was stirred at room temperature for 1 hour. The formed white precipitate was filtered, washed several times with DCM and dried. 13.96 g of 5-bromo-6-chloro-2-(methylsulfinyl)pyrimidine-4-amine were obtained (98.9%).

Workup

  1. filtrationThe formed white precipitate was filtered
  2. washwashed several times with DCM
  3. customdried

Sources & evidence

ORD record
ord-54da99abe4104ef5a9c928da98e967bc
Source dataset
uspto-grants-2016_09
Patent number
US09447095B2

Linked notes

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