3-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]prop-2-yn-1-ol → 3-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propan-1-ol
Reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]#[C:23][CH2:24][OH:25])=[CH:18][CH:17]=4)[CH:13]=[N:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(O)C.[OH-].[OH-].[Pd+2]>[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:20][CH:21]=4)[CH:13]=[N:12][C:11]=23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
A mixture of 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]prop-2-yn-1-ol (2-3, 1.48 g, 0.455 mmol) and 10% palladium hydroxide on carbon (2.0 g) in 2-propanol (500 mL) was stirred under a hydrogen balloon for 4.5 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated. The residue was purified by flash column chromatography (chloroform saturated with ammonia gas) to provide 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propan-1-ol (2-4) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ8.83 (s, 2H), 8.46 (s, 1H), 8.07 (br d, 2H, J=7.8 Hz), 7.54 (d, 2H, J=8.2 Hz), 7.47 (t, 2H, J=7.8 Hz), 7.38 (d, 2H, J=8.2 Hz), 7.29 (t, 1H, J=7.8 Hz), 3.73 (q, 2H, J=6.4 Hz), 2.81 (t, 2H, J=7.3 Hz), 1.95 (m, 2H), 1.30 (t, 1H, J=5.3 Hz).
Workup
- filtrationThe reaction mixture was filtered through celite
- concentrationthe filtrate was concentrated
- customThe residue was purified by flash column chromatography (chloroform saturated with ammonia gas)
Sources & evidence
- ORD record
- ord-311ea77b1c0b4d6fb121692b0fa399c7
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262199B2
Reaction notes
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