(3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methanol → 3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazole-4-carbaldehyde

HRID 539896Notes

Reaction equation

HRID 539896 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[CH:20]=[CH:19]4)[N:10]=2)[N:3]=1>ClCCl.O=[Mn]=O>[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[CH:20]=[CH:19]4)[N:10]=2)[N:3]=1

Participants

4

Reactant 1

HCID 86698985(3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 866989873-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazole-4-carbaldehydeYield 362%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of intermediate 7 (214 mg, 0.64 mmol) in 100 mL of dichloromethane (DCM), was added 58% of activated MnO2 (0.58 g, 6 equiv.). After being stirred for 12 hours at room temperature, the reaction mixture was passed through a pad of Celite and rinsed with dichloromethane. The filtrate was concentrated in vacuo to give desired intermediate 8 as a pale yellow solid (0.77 g, 36%); MS (ESI) m/z 333 [M+H]+

Workup

  1. washrinsed with dichloromethane
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f845c53f259549b9b71ca9dd730c8199
Source dataset
uspto-grants-2014_10
Patent number
US08871778B2

Reaction notes

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