N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine → 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-propylpyrazolo[1,5-a]pyridin-7-amine
Reaction equation
[CH2:1]([NH:4][C:5]1[N:10]2[N:11]=[C:12]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:15]=3)=[C:9]2[CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[H][H]>C(O)C.[Pd]>[CH2:21]([NH:20][C:16]1[N:15]=[C:14]([C:13]2[C:12]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)=[N:11][N:10]3[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[CH:6][CH:7]=[CH:8][C:9]=23)[CH:19]=[CH:18][N:17]=1)[CH2:22][CH2:23][CH3:24]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (80 mg, 0.19 mmol) in ethanol (5 mL) was added palladium on carbon (10%, 8 mg). The mixture was stirred overnight at room temperature under a balloon filled with hydrogen. The reaction was filtered through a pad of Celite and concentrated to give 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-propylpyrazolo[1,5-α]pyridin-7-amine (79 mg, 99%) as a gold foam. 1H NMR (CDCl3): δ 8.03 (d, 1H), 7.74 (d, 1H), 7.69 (m, 2H), 7.33 (t, 1H), 7.15 (t, 2H), 6.30 (d, 1H), 6.08–6.01 (m, 2H), 5.08 (broad, 1H), 3.47 (q, 2H), 3.37 (q, 2H), 1.87–1.41 (m, 6H), 1.08 (t, 3H), 0.99 (t, 3H); 19F NMR (CDCl3) δ −113.44; MS m/z 419 (M+1).
Workup
- filtrationThe reaction was filtered through a pad of Celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-996cd4497c054d44b71e738f65e090fc
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07163940B2
Reaction notes
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