Reaktion #331344

Reaktionsgleichung

trans-[3-(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-methanol

ammonia

dry ice acetone

→

title compound

trans-[3-(4-Amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)cyclobutyl]methanol

Lösungsmittel

dioxane

iPrOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigecondensed
2. 2
   Temperaturincreased by ≈2 mL
3. 3
   Sonstigethe tube was sealed
4. 4
   SonstigeThe solvents were evaporated
5. 5
   workup.ADDITIONwater was added to the residue
6. 6
   Filtrationthe pale yellow solid was filtered off
7. 7
   Sonstigedried in vacuo

Vorschrift

Gaseous ammonia (from a lecture bottle) was condensed into a suspension of trans-[3-(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-methanol (172.6 mg, 0.475 mmol) in dioxane (3 mL) and iPrOH (3 mL) in a sealable glass tube, cooled by dry ice/acetone, until the volume increased by ≈2 mL, then the tube was sealed and heated to 90° C. overnight. The solvents were evaporated, water was added to the residue, and the pale yellow solid was filtered off and dried in vacuo to give the title compound as a pale yellow solid. The compound was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 2.41-2.52 (m, 2H), 2.52-2.64 (m, 3H), 3.83 (d, J=6.3 Hz, 2H), 5.30-5.40 (m, 1H), 5.60 (brs, 2H), 7.29 (s, 1H), 8.26 (s, 1H). MS (ES+): m/z 345.1 (100) [MH+]. HPLC: tR=1.9 min (OpenLynx, polar—5 min).

Quelle