反应详情

温度

80 °C

A solution of tert-butyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (200 mg, 0.76 mmol) in EtOH (3.3 ml) was added to a solution of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA80, 100 mg, 0.30 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80° C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified using silica gel column chromatography [MeOH—CH2Cl2, 5:95] yielding BA81. BA81 was dissolved in 50:50 CH2Cl2:TFA and stirred for one hour at room temperature. The reaction mixture was concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81d. BA81d was dissolved in CH2Cl2 (2 ml) and BBr3 (4 mL, 4 mol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for 2 hours then concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81dd.

1. temperatureAfter cooling
2. extractionthe reaction was extracted with saturated NaCl and CH2Cl2
3. concentrationconcentrated in vacuo
4. custompurified
5. customyielding BA81
6. concentrationThe reaction mixture was concentrated in vacuo
7. custompurified
8. customto yield BA81d
9. stirringThe reaction was stirred at room temperature for 2 hours
10. concentrationthen concentrated in vacuo
11. custompurified
12. customto yield BA81dd