(4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol → 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

HRID 79138Notes

Reaction equation

HRID 79138 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

4

Reactant 1

HCID 59419388(4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol

Product 1

HCID 594193864-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehydeYield 82.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese(IV) oxide, <5 micron, activated (38.1 g, 439 mmol) was added to a solution of compound 223 (16.73 g, 87.8 mmol) in chloroform (800 mL). The reaction was stirred overnight, filtered through Celite, and the filtrate was concentrated in vacuo to yield compound 224 (13.7 g, 82.8% yield). 1H NMR (500 MHz, CDCl3) δ 10.31 (s, 1 H) 8.88 (s, 1 H) 2.65 (s, 2 H) ppm.

Workup

  1. filtrationfiltered through Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8ade62ae47844b1b97a849fa3f1c3b66
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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