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

HRID 599324Notes

Reaction equation

HRID 599324 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)Cl.O=[Mn]=O>[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 92%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of Example C1 (22.0 g, 119 mmol) and MnO2 (44 g, 506 mmol) in CHCl3 (300 mL) was stirred at RT for 3 h. The reaction was filtered and the filtrate was concentrated to give 4-(methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde as a pale solid (20 g, 92% yield). 1H NMR (400 MHz, DMSO-d6): 9.71 (s, 1 H), 8.60 (br s, 1 H), 8.49 (s, 1 H), 2.96 (d, J=4.8 Hz, 3 H), 2.48 (s, 3 H) MS (ESI) m/z: 184.0 (M+H+).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-11f5cafc8e824be8922ce21254f3d9a1
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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