2-Naphthol → 5-(Naphthalen-2-yloxymethyl)-furo[2,3-d]pyrimidine-2,4-diamine

Temperature

45 °C

To a 50 mL three neck round bottom flask was added in sequence anhydrous DMSO (4 mL), 2-naphthol (0.27 g), compound 117 (0.25 g) and anhydrous potassium carbonate (0.26 g). The reaction mixture was stirred at 45° C. for 24 h under nitrogen in the dark and then quenched with distilled water (12 mL). The resultant suspension was stirred at room temperature for 4 h, cooled to 5° C. and filtered. The sold was washed with cold water (2×5 mL) and then dissolved in MeOH. The solution was mixed with silica gel (1 g) and the mixture was evaporated under reduced pressure and dried in vacuo. The residue was ground into a fine powder and poured on top of a wet column of silica gel (30 g) and eluted with 3% MeOH in CHCl3. Fractions corresponding to a single spot of the product (TLC) were pooled and evaporated to afford 0.09 g compound 425 (23%) as a white solid.

1. customthen quenched with distilled water (12 mL)
2. stirringThe resultant suspension was stirred at room temperature for 4 h
3. temperaturecooled to 5° C.
4. filtrationfiltered
5. washThe sold was washed with cold water (2×5 mL)
6. dissolutiondissolved in MeOH
7. additionThe solution was mixed with silica gel (1 g)
8. customthe mixture was evaporated under reduced pressure
9. customdried in vacuo
10. additionpoured on top of a wet column of silica gel (30 g)
11. washeluted with 3% MeOH in CHCl3
12. customevaporated

ORD record

ord-57ff59ae93ee446cba62de71b1a511d3

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05958930