[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10](I)[C:3]=12.[CH3:12][Si:13]([CH3:17])([CH3:16])[C:14]#[CH:15].CN(C=O)C.C1COCC1>C(Cl)Cl.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:15]#[C:14][Si:13]([CH3:17])([CH3:16])[CH3:12])[C:3]=12Charge 4-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (5.4 g, 1.0 eq), trimethyl silyl acetylene (11.347 g, 6.0 eq), CuI (1.833 g, 0.5 eq), TEA (2.68 mL, 1.0 eq), DMF (67.5 mL), and THF (202.5 mL) in a round bottom flask under argon atmosphere. Stir the reaction mass under argon atm for 30 min. Charge (PPh3)4Pd (2.225 g, 0.1 eq) and stir the reaction mass at 35° C. for 3 h. Monitor the reaction by TLC (10% acetone in DCM). Concentrate the reaction mass under reduced pressure. Charge ethyl acetate and wash with saturated sodium bicarbonate solution, water and saturated aq. sodium chloride. Dry the organic layer over anhydrous sodium sulfate and concentrate the organic layer under reduced pressure. Purify the compound by column chromatography (silica 100-200 mesh, DCM-Acetone) to give desired product (1.81 g, 36.14%).
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