Hydrochloric Acid → HCID 22736336, compound

Participants

Reaction Steps

5M HCl (300 mL) was added slowly to a solution of 5-(4-amino-3-fluorophenyl)-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (18.49 g, 48.28 nmol) in acetone (800 mL) at 0° C. the resulting dark orange-brown solution was heated at 60° C. for 4 h. (t.l.c. analysis using 10% MeOH in CH2Cl2). The acetone was removed under reduced pressure and the acidic layer was basified to approx. pH 8 using sat. aq. Na2CO3. The resulting precipitate was collect by filtration and scrupulously dried to afford 4-[4-amino-5-(4-amino-3-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclohexanone as a light brown solid (12.67 g, 77%). A second crop was also obtained from the mother liquor on standing (2.01 g, 12%), 1H NMR (400 MHz, d6-DMSO) 2.27(2H, m), 2.30 (4H, br d), 2.73(2H, m), 5.14(1H, m), 5.20(2H, brs), 6.05(2H, brs), 6.85 (1H, t), 6.97(1H, dd), 7.06(1H, dd), 7.35(1H, s) and 8.12(1H, s) and m/z 340.1(MH+).

Provenance & Evidence