Réaction #79765

Équation de réaction

sodium bicarbonate

2-[4-(4-amino-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d)pyrimidin-5-yl)phenoxy]benzaldehyde

morpholine

sodium triacetoxyborohydride

→

5-[4-(2-morpholinomethylphenoxy)phenyl] -7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Solvants

1,2 dichloroethane

Conditions de réaction

Traitement

1. 1
   Filtrationthe mixture was filtered through an EMPORE® cartridge
2. 2
   AutreThe filtrate was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (5 ml)
4. 4
   workup.ADDITIONwere added
5. 5
   workup.STIRRINGthe mixture was stirred at ambient temperature overnight
6. 6
   AutreThe polymer was removed by filtration
7. 7
   Lavagewashed with dichloromethane
8. 8
   AutreThe combined organic filtrate and washings were evaporated under reduced pressure
9. 9
   Autreto give an oil which
10. 10
    Autrewas triturated with diethyl ether/ethyl acetate
11. 11
    Températurewith warming
12. 12
    workup.DISSOLUTIONto dissolve the solid
13. 13
    Températurethe solution was cooled in ice
14. 14
    Filtrationfiltered

Mode opératoire

A mixture of 2-[4-(4-amino-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d)pyrimidin-5-yl)phenoxy]benzaldehyde (0.15 g), morpholine (64 mg), sodium triacetoxyborohydride (117 mg) and 1,2 dichloroethane (5 ml) was stirred at ambient temperature for 18 hours. Saturated aqueous sodium bicarbonate solution was added and the mixture was filtered through an EMPORE® cartridge. The filtrate was evaporated and the residue was dissolved in dichloromethane (5 ml) and then tris(2-aminoethyl)amine-polymer bound (0.3 g) and 2 drops of glacial acetic acid were added and the mixture was stirred at ambient temperature overnight. The polymer was removed by filtration and washed with dichloromethane and then with methanol. The combined organic filtrate and washings were evaporated under reduced pressure to give an oil which was triturated with diethyl ether/ethyl acetate with warming to dissolve the solid and then the solution was cooled in ice and filtered to give 5-[4-(2-morpholinomethylphenoxy)phenyl] -7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 169-171° C.

Source