Réaction #1896906

Équation de réaction

{4-[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

thiophen-2-yl-methylamine

DavePhos

t-BuONa

→

{4-[3-{3-[(thiophen-2-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled
2. 2
   Filtrationfiltered
3. 3
   Autrethe filtrate was evaporated under reduced pressure
4. 4
   Autreto give the crude product
5. 5
   AutreIt was purified by chromatography (silica gel, 200-300 mesh, dichloromethane

Mode opératoire

To a stirred solution of {4-[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (from Example 39 supra) (300 mg, 0.48 mmol), thiophen-2-yl-methylamine (120 mg, 1.06 mmol), DavePhos (20 mg, 0.048 mmol) and t-BuONa (56 mg, 0.58 mmol) in 1,4-dioxane (10 mL), Pd2(dba)3 (28 mg, 0.48 mmol) was added in one portion under N2 atmosphere. The resultant mixture was stirred at 100° C. for 4 hours. The mixture was cooled and filtered; the filtrate was evaporated under reduced pressure to give the crude product. It was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH, 100:1, v/v) to give {4-[3-{3-[(thiophen-2-ylmethyl)-amino]-phenyl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 290 mg, 92.9%).

Source