(E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-prop-2-en-1-ol → (E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-propenal

HRID 403483Notes

Reaction equation

HRID 403483 reaction equation
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[CH2:23][OH:24])=[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]>C(#N)C.O=[Mn]=O>[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18](/[CH:21]=[CH:22]/[CH:23]=[O:24])=[CH:19][CH:20]=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 68378973(E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-prop-2-en-1-ol

Product 1

HCID 86671751(E)-3-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-propenal

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6342AcetonitrileSolvent

Procedure

(E)-3-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-prop-2-en-1-ol (6) (650 mg, 2.02 mmol), was dissolved in 20 ml acetonitrile. MnO2 (1.76 g, 20.2 mmol) was added and the black suspension was stirred at rt for 2.5 h. The reaction mixture was filtrated over celite and washed with acetonitrile. The filtrate was evaporated and purified by flash chromatography (silica gel, EtOAc/cHex (0-40%) to give a beige powder.

Workup

  1. filtrationThe reaction mixture was filtrated over celite
  2. washwashed with acetonitrile
  3. customThe filtrate was evaporated
  4. custompurified by flash chromatography (silica gel, EtOAc/cHex (0-40%)
  5. customto give a beige powder

Sources & evidence

ORD record
ord-a60324abc43b457891e698f3c2908168
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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