Reaktion #92171

Reaktionsgleichung

6-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

(3-chlorophenyl)boronic acid

K3PO4

→

6-(3-chlorophenyl)-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetra hydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Ausbeute 76.4%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to RT
2. 2
   Filtrationfiltered
3. 3
   TrocknenThe organic layer was dried over Na2SO4
4. 4
   Einengenconcentrated to a residue which
5. 5
   Sonstigewas purified by chromatography
6. 6
   Wascheneluted with PE/EA (10:1 to 3:1)

Vorschrift

To a solution of 6-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (50 mg, 0.091 mmol), (3-chlorophenyl)boronic acid (28.7 mg, 0.183 mmol) and aq. 2 M K3PO4 (0.4 mL) in dioxane (2 mL) was added Pd(PPh3)4 (10 mg). The reaction was heated at 85° C. for 2 h, cooled to RT, filtered and the filtrate was diluted DCM (10 mL) and water (10 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (10:1 to 3:1) to give 6-(3-chlorophenyl)-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetra hydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (40 mg, 75.6% yield) as a solid. LCMS: [M+-THP-OH] 473 and TR=2.215 min.

Quelle