Reaktion #88723

Reaktionsgleichung

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

K3PO4

2-isopropylphenylboronic acid

→

5-((4-chloro phenyl) (hydroxy)methyl)-6-(2-isopropylphenyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Ausbeute 93.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to RT
2. 2
   Filtrationfiltered
3. 3
   ExtraktionThe filtrate was extracted with EA (2×20 mL)
4. 4
   WaschenThe combined organic layers were washed with water (20 mL) and brine (15 mL)
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated to a residue which
7. 7
   Sonstigewas purified by Prep TLC
8. 8
   Wascheneluted with PE/EA (1:1)

Vorschrift

To a mixture of 6-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (50 mg, 0.093 mmol), Pd(dppf)Cl2 (7 mg, 0.01 mmol) and aq. 2N K3PO4 (0.4 mL) in dioxane (2 mL) was added 2-isopropylphenylboronic acid (30 mg, 0.183 mmol). The reaction was heated at 80° C. for 18 h, cooled to RT and filtered. The filtrate was extracted with EA (2×20 mL). The combined organic layers were washed with water (20 mL) and brine (15 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep TLC eluted with PE/EA (1:1) to give 5-((4-chloro phenyl) (hydroxy)methyl)-6-(2-isopropylphenyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (50 mg, 93% yield) as a white solid.

Quelle