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

HRID 3221

Reaction equation

HRID 3221 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][OH:11])=[CH:8][N:7]=[C:6]([S:12][CH3:13])[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]([S:12][CH3:13])[N:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 10584149(4-(Ethylamino)-2-(methylthio)pyrimidin-5-yl)methanol

Product 1

HCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehydeYield 97.8%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalyst2×HCID 6212ChloroformSolvent

Procedure

To 4-ethylamino-2-methylthio-5-pyrimidinemethanol (6.44 g, 32.4 mmol) in 600 mL of chloroform was added manganese oxide (21.0 g, 241 mmol) over 3 minutes. The suspension was stirred at room temperature for 2 hours, and an additional 5.5 g of manganese oxide was added. Stirring was continued for 4.5 hours. The mixture was then filtered through celite washing with chloroform. The filtrate was concentrated in vacuo to give 6.25 g (97%) of 4-ethylamino-2-methylthio-5-formylpyrimidine; mp 58°-61° C.

Workup

  1. stirringStirring
  2. waitwas continued for 4.5 hours
  3. filtrationThe mixture was then filtered
  4. washthrough celite washing with chloroform
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0f80dab124bd4936956f14f0363292fa
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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