1-Naphthylamine → 5-[(1-Naphthylamino)methyl]furo[2,3-d]pyrimidine-2,4-diamine

Temperature

50 °C

To a 50 ml three neck round bottom flask was added sequentially anhydrous DMSO (5 ml), 1-aminonaphthalene (0.66 g), Compound 117 (0.50 g) and anhydrous potassium carbonate (0.69 g). The reaction mixture was stirred at 50° C. for 8 h under nitrogen in the dark. The reaction was then quenched with distilled water (15 ml) and the resultant suspension stirred at room temperature for 4 h, cooled to 5° C. and filtered. The residue was washed with cold water (2×5 ml) and then dissolved in hot MeOH, and the solution mixed with silica gel (2 g). The mixture was evaporated under reduced pressure and then dried in vacuo. The residue was ground into a fine powder and poured on top of a dry column of silica gel (40 g). The column was washed with MeOH in CHCl3: 200 ml (0.5%), 100 ml (1%), 100 ml (2%). The column then eluted with 3% MeOH in CHCl3. Fractions corresponding to a single spot of the product (TLC) were pooled and evaporated. The residue was washed with ether and air dried to afford 0.25 g (33%) of compound 423 as a light yellow solid.

1. customThe reaction was then quenched with distilled water (15 ml)
2. stirringthe resultant suspension stirred at room temperature for 4 h
3. temperaturecooled to 5° C.
4. filtrationfiltered
5. washThe residue was washed with cold water (2×5 ml)
6. dissolutiondissolved in hot MeOH
7. additionthe solution mixed with silica gel (2 g)
8. customThe mixture was evaporated under reduced pressure
9. customdried in vacuo
10. additionpoured on top of a dry column of silica gel (40 g)
11. washThe column was washed with MeOH in CHCl3
12. washThe column then eluted with 3% MeOH in CHCl3
13. customevaporated
14. washThe residue was washed with ether and air
15. customdried

ORD record

ord-c0f31d0984164a0ba7fbf34ac639d5e4

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06537999B2