Methylamine → 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-methylpyrazolo[1,5-a]pyridin-7-amine
Reaction equation
[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[C:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[N:14][N:15]3[C:20](Cl)=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:29][NH2:30]>>[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[C:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[N:14][N:15]3[C:20]([NH:30][CH3:29])=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
In a similar manner as described in Example 14, from N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (53 mg, 0.13 mmol) and methylamine (5 mL, 40% aqueous) in a sealed tube was obtained 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-methylpyrazolo[1,5-α]pyridin-7-amine (40.5 mg, 77%) as a pale yellow solid. 1H NMR (CDCl3): δ 8.01 (d, 1H), 7.75 (d, 1H), 7.62 (m, 2H), 7.34 (t, 1H), 7.13 (t, 2H), 6.30 (d, 1H), 6.03–5.99 (m, 2H), 5.11 (broad, 1H), 3.46 (q, 2H), 3.10 (d, 3H), 1.69–1.42 (m, 4H), 0.97 (t, 3H); 19F NMR (CDCl3) δ −113.39; MS m/z 391 (M+1).
Sources & evidence
- ORD record
- ord-4cdefbb49e2b4be9a5ef4a63896b6a8c
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07163940B2
Reaction notes
Loading…