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

HRID 599330Notes

Reaction equation

HRID 599330 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]>O=[Mn]=O>[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

3

Reactant 1

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

Product 1

HCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehydeYield 94.6%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

Activated MnO2 (52 g, 0.6 mol) was added to a solution of (4-(ethylamino)-2-(methylthio)pyrimidin-5-yl)methanol (15 g, 0.075 mol) in CH2CL2 (300 mL) and the reaction mixture was stirred overnight at RT. The reaction solution was filtered and the filtrate was concentrated to give 4-(ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (14 g, 93% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.71 (s, 1 H), 8.67 (br s, 1 H), 8.49 (s, 1 H), 3.51 (m, 2 H), 2.48 (s, 3 H), 1.17 (t, J=7.2 Hz, 3 H).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-69f06555b8b34a928a50535f7d051fff
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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