Reaktion #79758

Reaktionsgleichung

Sodium hydride

4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine

3-(tosyloxy) tetrahydrofuran

→

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

Lösungsmittel

dimethylformamide

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 30 minutes
2. 2
   workup.STIRRINGwith stirring
3. 3
   workup.STIRRINGThe mixture was stirred
4. 4
   Sonstigeevaporated under vacuum
5. 5
   SonstigeThe residue was partitioned between ethyl acetate and water
6. 6
   SonstigeThe ethyl acetate layer was separated
7. 7
   Sonstigedried
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto give a residual gummy solid which
10. 10
    Sonstigewas triturated with ether
11. 11
    Filtrationfiltered

Vorschrift

Sodium hydride (120 mg, of a 60% dispersion in mineral oil) was added to a solution of 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (906 mg) and dimethylformamide (30 ml) with stirring under nitrogen. The mixture was stirred for 30 minutes and then a solution of 3-(tosyloxy) tetrahydrofuran (750 mg) in dimethyl formamide (10 ml) was added with stirring. The mixture was stirred and heated at 95° C. for 18 hours and then evaporated under vacuum. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried and evaporated to give a residual gummy solid which was triturated with ether and filtered to give 5-(4-phenoxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine m.p. 196-196.5° C.

Quelle