Reaktion #325145

Reaktionsgleichung

Na2CO3

2,3-dihydro-1,4-benzodioxin-6-ylboronic acid

3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

→

3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Ausbeute 15.0%

Lösungsmittel

EtOH

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Extraktionthe reaction was extracted with saturated NaCl and CH2Cl2
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigepurified by RP-HPLC (MeCN:H2O:0.1% TFA)
5. 5
   Sonstigeto yield BA54 (6 mg, 15% yield)

Vorschrift

A solution of 2,3-dihydro-1,4-benzodioxin-6-ylboronic acid (26 mg, 0.14 mmol) in EtOH (3.3 mL) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (40 mg, 0.13 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 by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA54 (6 mg, 15% yield). ESI-MS (M+H)+ m/z calcd 312.1, found 312.0.

Quelle