(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
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
Product 1
Reagents, catalysts & solvents 2
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.