Acetonitrile → HCID 86719408, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (R,E)-1-(3-(4-amino-6-nitro-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidin-1-yl)-4-(cyclopropyl(methyl)amino)but-2-en-1-one (160) (227 mg, 0.41 mmol) in THF/MeOH/H2O (4 mL/2 mL/1 mL) was added iron powder (92 mg, 1.64 mmol) and NH4Cl (89 mg, 1.64 mmol). The resulting mixture was heated at 50° C. for 1 hrs under N2, and then filtered through a pad of Celite. The filtrate was directly loaded and purified by preparative HPLC (RP, C18, 10 to 95% acetonitrile in water (0.1% HCOOH)) to give (R,E)-4-(cyclopropyl(methyl)amino)-1-(3-(4,6-diamino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidin-1-yl)but-2-en-1-one (162) (12 mg, 6% yield) as a white solid. LC-MS (ESI): m/z (M+1) 524.1. 1H NMR (400 MHz, DMSO) δ 8.21 (s, 1H), 7.91 (d, J=6.4 Hz, 1H), 7.40 (t, J=7.8 Hz, 2H), 7.32 (d, J=5.6 Hz, 2H), 7.14 (t, J=7.2 Hz, 1H), 7.07 (t, J=6.9 Hz, 3H), 6.74-6.57 (m, 1H), 6.38 (dd, J=31.6, 15.5 Hz, 1H), 5.51 (s, 2H), 5.25 (d, J=11.5 Hz, 2H), 5.17-4.96 (m, 1H), 4.35-3.45 (m, 4H), 3.29-3.20 (m, 3H), 3.09-2.94 (m, 1H), 2.22 (d, J=15.3 Hz, 3H), 1.76-1.61 (m, 1H), 0.47-0.34 (m, 2H), 0.34-0.22 (m, 2H).

Provenance & Evidence