Sodium hydride → HCID 86667959, compound

Reaction equation

[H-].[Na+].[Br:3][C:4]1[N:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][C:15]([Cl:19])=[N:16][CH:17]=3)[NH:12][N:11]=2)[CH:7]=[CH:6][CH:5]=1.Cl[CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[Br:3][C:4]1[N:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][C:15]([Cl:19])=[N:16][CH:17]=3)[N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:11]=2)[CH:7]=[CH:6][CH:5]=1

Participants

Procedure

To a mixture of NaH (1.3 mg, 37.6 mmol, 60%) in DMF (80 mL) was added slowly the solution of crude 3-(6-bromo-pyridin-2-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine (from Example 30 supra) (5.83 g, 18.8 mmol) in DMF (40 mL) at 5° C. The ice-bath was removed and the mixture was stirred for 20 minutes. Then (2-(chloromethoxy)ethyl)trimethylsilane (4.06 g, 24.4 mmol) was added. This solution was stirred for 12 hours at room temperature. The solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous NH4Cl and dichloromethane (3×20 mL). The combined organics was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 60 g, 200-300 mesh, eluting with ethyl acetate:petroleum ether, 1:10) to give 3-(6-bromo-pyridin-2-yl)-6-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine as a white solid. (Yield 4.9 g, 84%).