Réaction #73104

Équation de réaction

(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

NaHCO3

→

title compound

Rendement 80.0%

(R)-8-cyclopentyl-7-ethyl-2-(2-hydroxypyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

Rendement 80.0%

Solvants

HCOOH

Conditions de réaction

Traitement

1. 1
   TempératureThis mixture was heated
2. 2
   Températureto reflux for 18 h
3. 3
   Extractionthe mixture was extracted with EtOAc
4. 4
   SéchageThe combined organic phase was dried with Na2SO4
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   Autrechromatographed on flash silica gel (CH2Cl2:CH3OH=6:1)

Mode opératoire

(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 100 mg, 0.28 mmol) was dissolved in 3 mL of HCOOH. This mixture was heated to reflux for 18 h, then aqueous NaHCO3 was added and the mixture was extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure and chromatographed on flash silica gel (CH2Cl2:CH3OH=6:1) to give the title compound as a white solid (80 mg, 80% yield). 1H NMR (CD3OD) δ: 8.09 (s, 1H), 8.52 (d, 1H) 7.46 (s, 1H), 7.27 (m, 1H), 4.42-4.38 (m, 2H), 3.41 (s, 3H), 2.0-1.7 (m, 10H) and 0.86 ppm (t, 3H); LCMS: 354.2 m/z (M+H)+; ret. Time: 1.36 min (Analytical Method E).

Source