Reaktion #79806

Reaktionsgleichung

tert-butyl 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-pyrrolidinecarboxylate

trifluoroacetic acid

→

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

Ausbeute 79.2%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   workup.ADDITIONdilute NaOH added (5N, 10 ml)
3. 3
   ExtraktionThe resulting residue solution was extracted with EtOAc (3×50 ml)
4. 4
   Waschenthe combined organics were washed with brine (1×75 ml)
5. 5
   TrocknenThe organic solution was dried (sodium sulphate)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated in vacuo

Vorschrift

To a solution of tert-butyl 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-pyrrolidinecarboxylate (0.8 g, 1.7 mmol) in dichloromethane (25 ml) at 0° C. was added trifluoroacetic acid (5 ml). The reaction mixture was warmed to room temperature and stirred at room temperature for 20 hr. The solvent was evaporated and dilute NaOH added (5N, 10 ml). The resulting residue solution was extracted with EtOAc (3×50 ml) and the combined organics were washed with brine (1×75 ml). The organic solution was dried (sodium sulphate), filtered and evaporated in vacuo to leave 5-(4-phenoxyphenyl)-7-(3-pyrrolidinyl) -7H-pyrrolo[2,3-d]pyrimidin-4-ylamine as a white solid (0.5 g, 79%) m.pt. 182-184° C. Rf in 1:1 EtOAc : MeOH=0.15. 1H NMR (d6 DMSO, 250 MHz): 8.14 (1H, s), 7.37-7.50 (5H, m), 7.05-7.18 (5H, m), 6.14 (2H, bs), 5.23 (1H, m), 3.09-3.27 (2H, m), 2.83-2.98 (2H, m), 2.19-2.33 (1H, m), 1.88-2.01 (1H, m). Mass spec. 371.1758 (C22H2 ON5). IR (KBr disc): 3106, 1585, 1489, 1232 cm−1.

Quelle