{1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazol-4-yl}-methanol → 1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carbaldehyde

HRID 403495Notes

Reaction equation

HRID 403495 reaction equation
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([CH2:26][OH:27])[C:23]([CH3:28])=[N:22]3)=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([CH:26]=[O:27])[C:23]([CH3:28])=[N:22]3)=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68378977{1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazol-4-yl}-methanol

Product 1

HCID 866717551-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

{1-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazol-4-yl}-methanol (18) (500 mg, 1.38 mmol) was dissolved in 10 ml of dichloromethane and after addition of manganese dioxide (1.2 g, 13.8 mmol) the reaction mixture was stirred for 3 h at rt. The mixture was filtrated though celite and evaporated under reduced pressure. The product was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtrated though celite
  2. customevaporated under reduced pressure
  3. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-f08f5c0ab5e341139d5f0a004898ef11
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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