Reaktion #92175

Reaktionsgleichung

6-bromo-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

3,4-dichlorophenylboronic acid

K3PO4

→

6-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Ausbeute 27.4%

Lösungsmittel

dioxane

EA

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to RT
2. 2
   WaschenThe organic layer was washed with brine (20 mL) and aq. NH4Cl (20 mL)
3. 3
   Trocknendried with Na2SO4
4. 4
   Einengenconcentrated to a residue which
5. 5
   Sonstigewas purified by Prep HPLC

Vorschrift

To a solution of 6-bromo-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (50 mg, 0.15 mmol) in dioxane (2 mL) was added 3,4-dichlorophenylboronic acid (57.3 mg, 0.3 mmol), Pd(PPh3)4 (17.3 mg, 0.015 mmol) and aq. 2M K3PO4 (0.4 mL). The reaction was heated at 85° C. for 1 h, cooled to RT then diluted with EA (20 mL). The organic layer was washed with brine (20 mL) and aq. NH4Cl (20 mL), dried with Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 6-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (15.0 mg, 27.4% yield) as a white solid. 1H NMR (CDCl3) δ: 7.55-7.48 (m, 2H), 7.24 (d, J=2.1 Hz, 1H), 4.27-4.14 (m, 2H), 3.60-3.50 (m, 5H), 3.27 (t, J=6.5 Hz, 1H), 2.54 (s, 3H), 2.00-1.85 (m, 2H). LCMS: MH+ 399 and TR=3.000 min.

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