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

HRID 1893891Notes

Reaction equation

HRID 1893891 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-9a7fd0f1803547b58b5240f6a42e52f1
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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