[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][CH:22]=[CH:23][C:16]=23)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.[H-].[K+].I[CH3:27].Cl>CN(C)C=O.C(OCC)C.CCCCCC>[CH3:27][N:21]1[C:17]2=[N:18][CH:19]=[CH:20][C:15]([C:8]3[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:11][N:10]4[CH2:12][CH2:13][CH2:14][C:9]=34)=[C:16]2[CH:23]=[CH:22]1Dissolve 4-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (Example 1; 0.150 g, 0.50 mmol) in N,N-dimethylformamide (10 ml). Add n-hexane (2 mL) and cool to 0° C. Add potassium hydride (35% suspension in mineral oil, 0.12 g, 1.0 mmol) and stir under nitrogen at 0° C. for 5 min. Add iodomethane (0.18 g, 1.3 mmol) and stir at 0° C. for 15 min. Dilute the reaction mixture by adding 1.0M aqueous hydrochloric acid (10 mL) and with excess diethyl ether. Extract the mixture with 0.2M aqueous hydrochloric acid. Combine the acidic aqueous extracts, add 5M aqueous sodium hydroxide until basic, and extract with dichloromethane. Concentrate the organic extracts under reduced pressure and purify via chromatography (silica gel, 95% ethyl acetate/5% methanol containing 0.1M ammonia) to obtain 0.125 g (79%) of the title compound as a cream colored solid. TOF MS (ES) exact mass calculated for C19H18N5 (p+H): m/z=316.1562, Found: 316.1536.
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