Triphenyl phosphite → 4-[2-[4-(t-Butyl)phenyl]ethoxy]pteridine

Temperature

10 °C

To a suspension of 2 g of 4-hydroxypteridine in 20 mL of CH2Cl2 under nitrogen was added 1.2 g of pyridine. The mixture was cooled to -30° C. and over a 15 minute period a solution of 4.82 g of triphenyl phosphite in CH2Cl2 was added simultaneously with addition of chlorine gas. The mixture was stirred for one and one half hours while maintaining the temperature at -15° to -20° C. The mixture was then allowed to warm to 10° C., and a solution of 2.67 g of 2-[4-(t-butyl)phenyl]ethanol in CH2Cl2 was added. The resulting mixture was refluxed for 45 minutes, then cooled and diluted into toluene. The toluene solution was washed with dilute base, then filtered through phase separating paper and concentrated in vacuo. The resulting bluish oil was adsorbed onto silica gel and chromatographed (silica gel, CH2Cl2 →80% CH2Cl2, 20% EtOAc). Fractions containing the major product were combined. The product was then recrystallized from petroleum ether/CH2Cl2. Yield 60 mg. M.P. 149° C.

1. temperaturewhile maintaining the temperature at -15° to -20° C
2. temperatureThe resulting mixture was refluxed for 45 minutes
3. temperaturecooled
4. washThe toluene solution was washed
5. additionwith dilute base
6. filtrationfiltered through phase
7. customseparating paper
8. concentrationconcentrated in vacuo
9. customchromatographed (silica gel, CH2Cl2 →80% CH2Cl2, 20% EtOAc)
10. additionFractions containing the major product
11. customThe product was then recrystallized from petroleum ether/CH2Cl2

ORD record

ord-99d8239b548343e0849d911e6be2e38d

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05350749