m-Chloroperbenzoic acid → 5-bromo-6-chloro-2-(methylsulfinyl)-N-(prop-2-ynyl)pyrimidine-4-amine

HRID 63607Notes

Reaction equation

HRID 63607 reaction equation
[Br:1][C:2]1[C:3]([NH:11][CH2:12][C:13]#[CH:14])=[N:4][C:5]([S:9][CH3:10])=[N:6][C:7]=1[Cl:8].ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[Br:1][C:2]1[C:3]([NH:11][CH2:12][C:13]#[CH:14])=[N:4][C:5]([S:9]([CH3:10])=[O:23])=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 903037135-bromo-6-chloro-2-(methylthio)-N-(prop-2-ynyl)pyrimidine-4-amine2×

Product 1

HCID 903037735-bromo-6-chloro-2-(methylsulfinyl)-N-(prop-2-ynyl)pyrimidine-4-amineYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 5-bromo-6-chloro-2-(methylthio)-N-(prop-2-ynyl)pyrimidine-4-amine (intermediate 29) (5.45 mmol) in 6 ml of DCM, 1.34 g (6 mmol) of m-chloroperbenzoic acid (77%) (Aldrich) in 8 ml of DCM were added dropwise. The reaction mixture was stirred at room temperature for 1 hour. The precipitate was filtered, washed several times with cold DCM and dried. 1.52 g (90.5%) of 5-bromo-6-chloro-2-(methylsulfinyl)-N-(prop-2-ynyl)pyrimidine-4-amine were obtained as a light brown solid.

Workup

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

Sources & evidence

ORD record
ord-9f43d62f7c9347409fe42e65461f17c5
Source dataset
uspto-grants-2016_09
Patent number
US09447095B2

Reaction notes

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