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

HRID 2274169Notes

Reaction equation

HRID 2274169 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-ad00d2fb88c043dbaa1abb5a2b7f66b2
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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