Water → 2-(5-Bromo-2-(methylsulfonyl)pyrimidin-4-yl)thiazolo[5,4-c]pyridine

HRID 2267320Notes

Reaction equation

HRID 2267320 reaction equation
[OH:1]OS([O-])=O.[K+].[Br:7][C:8]1[C:9]([C:16]2[S:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[N:24]=2)=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1.[OH2:25]>ClCCl>[Br:7][C:8]1[C:9]([C:16]2[S:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[N:24]=2)=[N:10][C:11]([S:14]([CH3:15])(=[O:1])=[O:25])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 574288282-(5-Bromo-2-(methylthio)pyrimidin-4-yl)thiazolo[5,4-c]pyridine

Product 1

HCID 602043722-(5-Bromo-2-(methylsulfonyl)pyrimidin-4-yl)thiazolo[5,4-c]pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of oxone (179 mg, 0.29 mmol) in water (10 mL) was added dropwise to a stirred solution of 2-(5-bromo-2-(methylthio)pyrimidin-4-yl)thiazolo[5,4-c]pyridine (66 mg, 0.19 mmol) in dichloromethane (12 mL) at 0° C. The bright yellow suspension was allowed to warm to r.t. overnight. After 14 h the organic layer was separated, dried over sodium sulfate, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography (ethyl acetate/hexane 25:75 to 50:50) to yield 2-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)thiazolo[5,4-c]pyridine (59 mg, 82%) as a white amorphous solid. 1H NMR: δ (CDCl3, 400 MHz) 3.47 (s, 3 H), 8.13 (d, J=5.5 Hz, 1 H), 8.79 (d, J=5.5 Hz, 1 H), 9.29 (s, 1 H), 9.39 (s, 1 H).

Workup

  1. customAfter 14 h the organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by flash chromatography (ethyl acetate/hexane 25:75 to 50:50)

Sources & evidence

ORD record
ord-37d6c3d05eac4999ab170f4f21709598
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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