[4-(Ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl]methanol → 4-(Ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde

HRID 1666253Notes

Reaction equation

HRID 1666253 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([CH3:12])[N:7]=[C:6]([S:13][CH3:14])[N:5]=1)[CH3:2]>C(Cl)(Cl)Cl.[O-2].[Mn+2]>[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=[O:11])=[C:8]([CH3:12])[N:7]=[C:6]([S:13][CH3:14])[N:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 57606985[4-(Ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl]methanol

Product 1

HCID 576069534-(Ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehydeYield 93.6%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalyst2×HCID 6212ChloroformSolvent

Procedure

To a solution of [4-(ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl]methanol (41.0 g) in chloroform (4000 mL) was added manganese oxide (125 g, 1.4 mole) and stirred for 4 h at room temperature. More manganese oxide was added until the disappearance of alcohol compound was observed. The reaction mixture was filtered through Celite and washed with some chloroform and evaporated all organic solvents to give 38 g (92% yield) of 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde as a colorless solid, which was used without purification in the next step.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with some chloroform
  3. customevaporated all organic solvents

Sources & evidence

ORD record
ord-4f934987f5124f18b77249a762386bb5
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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