(4-Ethylamino-2-phenylamino-pyrimidin-5-yl)methanol → 4-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

HRID 2300054Notes

Reaction equation

HRID 2300054 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][OH:11])=[CH:8][N:7]=[C:6]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[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])=[CH:8][N:7]=[C:6]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 10681743(4-Ethylamino-2-phenylamino-pyrimidin-5-yl)methanol

Product 1

HCID 108240804-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehydeYield 99%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of (4-ethylamino-2-phenylamino-pyrimidin-5-yl)-methanol (173 mg, 0.71 mmol) in 15 mL of chloroform was added manganese oxide (600 mg, 6.89 mmol). After stirring at room temperature overnight, the mixture was filtered through a pad of celite, washing with chloroform. The filtrate was concentrated in vacuo to give 170 mg (99%) of 4-ethylamino-2-phenylamino-pyrimidine-5-carboxaldehyde, mp 155-157° C.

Workup

  1. filtrationthe mixture was filtered through a pad of celite
  2. washwashing with chloroform
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-79687832cbc64a329f505e0cad053445
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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