Reaktion #92189

Reaktionsgleichung

methyl 3-(6-bromo-1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate

4-chlorophenylboronic acid

Cs2CO3

→

methyl 3-(6-(4-chlorophenyl)-1,5-dimethyl-2,4-dioxo-1,2-dihydro thieno[2,3-d]pyrimidin-3(4H)-yl)propanoate

Ausbeute 46.5%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was degassed under nitrogen gas (3×)
2. 2
   workup.ADDITIONPd(PPh3)4 (10 mg) was added
3. 3
   Temperaturcooled to RT
4. 4
   workup.ADDITIONthen diluted with EA (10 mL)
5. 5
   WaschenThe organic layer was washed with brine (10 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated to a residue which
8. 8
   Sonstigewas purified by chromatography
9. 9
   Wascheneluted with DCM/MeOH (80:1)

Vorschrift

To a solution of methyl 3-(6-bromo-1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (180 mg, 0.498 mmol) in toluene (5 mL) was added 4-chlorophenylboronic acid (78 mg, 0.498 mmol) and aq. Cs2CO3 solution (1 M, 1 mL). The reaction was degassed under nitrogen gas (3×) then Pd(PPh3)4 (10 mg) was added. The reaction was heated at 100° C. for 18 h, cooled to RT then diluted with EA (10 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with DCM/MeOH (80:1) to give methyl 3-(6-(4-chlorophenyl)-1,5-dimethyl-2,4-dioxo-1,2-dihydro thieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (91 mg, 46.5% yield) as a yellow solid. LCMS: MH+ 393 and TR=1.956 min.

Quelle