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

HRID 2404008Notes

Reaction equation

HRID 2404008 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][NH:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1

Participants

4

Reactant 1

HCID 10679092(4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol

Product 1

HCID 106075204-(Methylamino)-2-(methylthio)pyrimidine-5-carbaldehydeYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (3.1 g, 16.73 mmol) and manganese dioxide (7.27 g, 83.67 mmol) in DCM (40 mL) was stirred at room temperature for 12 hours. The resulting precipitate was filtered off, and the filtrate was concentrated to give 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (2.8 g, 91%) as a yellowish solid. MS (ES+) C7H9N3OS requires: 183. found: 184 [M+H]+.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-77be44073452485599df9c5a80764a08
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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