Sodium ethoxide → N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine
Reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]([C:11](=O)[C:12]#[CH:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1.S(O)(O)(=O)=O.[CH2:27]([NH:31][C:32]([NH2:34])=[NH:33])[CH2:28][CH2:29][CH3:30].[O-]CC.[Na+]>>[CH2:27]([NH:31][C:32]1[N:34]=[C:11]([C:10]2[C:9]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[N:8][N:7]3[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=23)[CH:12]=[CH:13][N:33]=1)[CH2:28][CH2:29][CH3:30]Participants
4
Procedure
In a similar manner as described in Example 34 from 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (0.50 g, 1.7 mmol), N-butylguanidine sulfate and sodium ethoxide (0.81 mL, 21 wt % in ethanol, 2.2 mmol) at room temperature was obtained N-butyl-4-[7-chloro-2-(4-fluorophenyl)-pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (0.39 g, 59% o) as a fluffy pale yellow solid. 1H NMR (CDCl3): δ 8.40 (d, 1H), 8.07 (d, 1H), 7.65 (m, 2H), 7.29 (m, 1H), 7.15 (t, 2H), 7.06 (d, 1H), 6.32 (d, 1H), 5.16 (bs, 1H), 3.49 (q, 2H), 1.71–1.41 (m, 4H), 0.99 (t, 3H); 19F NMR (CDCl3) δ−112.77; MS m/z 396 (M+1).
Sources & evidence
- ORD record
- ord-d0c724469e054bcd98bb5c77593ab006
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109209B2
Reaction notes
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