反応 #79765

反応方程式

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

溶媒

1,2 dichloroethane

反応条件

後処理

1. 1
   ろ過the mixture was filtered through an EMPORE® cartridge
2. 2
   その他The 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
   その他The polymer was removed by filtration
7. 7
   洗浄washed with dichloromethane
8. 8
   その他The combined organic filtrate and washings were evaporated under reduced pressure
9. 9
   その他to give an oil which
10. 10
    その他was triturated with diethyl ether/ethyl acetate
11. 11
    温度with warming
12. 12
    workup.DISSOLUTIONto dissolve the solid
13. 13
    温度the solution was cooled in ice
14. 14
    ろ過filtered

実験手順

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.

出典