Reaktion #79848

Reaktionsgleichung

trans-5-(4-chloro-7-(4-(4-methylpiperazino)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-phenoxybenzonitrile

ammonium hydroxide

→

5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxybenzonitrile bisacetate

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen cooled
2. 2
   Sonstigeevaporated under reduced pressure
3. 3
   SonstigeThe residue was purified by preparative RP-HPLC

Vorschrift

A mixture of trans-5-(4-chloro-7-(4-(4-methylpiperazino)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-phenoxybenzonitrile (150 mg) in 1,4-dioxane (25 mL) and 30% aqueous ammonium hydroxide (25 mL) was heated at 120° C. in a sealed tube for 18 hours then cooled and evaporated under reduced pressure. The residue was purified by preparative RP-HPLC to give 5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxybenzonitrile bisacetate: 1H NMR (DMSO-d6, 400 MHz) δ 8.14(s, 1H), 7.91(s, 1H), 7.70(d, 1H), 7.55(s, 1H), 7.48(t, 2H), 7.27(t, 1H), 7.20(d, 2H), 7.06(d, 1H), 6.27(bs, 2H), 4.55 (m, 1H), 2.53 m, 4H), 2.36(m, 5H), 2.17 (s, 3H), 2.0(m, 6H), 1.96(s, 6H); MS MH+508.3; RP-HPLC (Hypersil HS, 5 μm, 100 A, 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 7.27 min.

Quelle