تفاعل #79765

معادلة التفاعل

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

المذيبات

1,2 dichloroethane

ظروف التفاعل

المعالجة

1. 1
   ترشيحthe mixture was filtered through an EMPORE® cartridge
2. 2
   أخرىThe 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
   أخرىThe polymer was removed by filtration
7. 7
   غسيلwashed with dichloromethane
8. 8
   أخرىThe combined organic filtrate and washings were evaporated under reduced pressure
9. 9
   أخرىto give an oil which
10. 10
    أخرىwas triturated with diethyl ether/ethyl acetate
11. 11
    درجة الحرارةwith warming
12. 12
    workup.DISSOLUTIONto dissolve the solid
13. 13
    درجة الحرارةthe solution was cooled in ice
14. 14
    ترشيحfiltered

الإجراء التجريبي

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.

المصدر