[4-Amino-2-(methylsulfanyl)pyrimidin-5-yl]methanol → 4-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

HRID 1984619Notes

Reaction equation

HRID 1984619 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

4

Reactant 1

HCID 220531[4-Amino-2-(methylsulfanyl)pyrimidin-5-yl]methanol

Product 1

HCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To the solution of 4-amino-5-hydroxymethyl-2-(methylthio)pyrimidine (1.0 g, 5.84 mmol) in CHCl3 (100 mL) was added MnO2 (2.5 g, 29.2 mmol, 5 equiv). The suspension was stirred at rt overnight. The mixture was filtered through celite and washed with CHCl3. The combined filtrate was concentrated to give the titled compound. 1H-NMR (500 MHz, CDCl3) δ 9.78 (s, 1H), 8.42 (s, 1H), 8.20 (broad, 1H), 5.74 (broad, 1H)), 2.55 (3, 3H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with CHCl3
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-3f5a2a933d054a059bf522809dccce11
Source dataset
uspto-grants-2009_06
Patent number
US07544677B2

Reaction notes

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