Formic Acid → HCID 59024003, compound

Participants

Reaction Steps

A solution of {3-[(2-amino-pyrimidin-4-yl)-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-amino]-propyl}-carbamic acid benzyl ester (prepared from Example #F.8.1 using general procedures O and N, 0.169 g, 0.308 mmol) and formic acid (0.116 mL, 3.08 mmol) in methanol (2 mL) was added dropwise to a suspension of Palladium black (0.080 g, 0.752 mmol) in methanol (1.5 mL). The resulting mixture was allowed to stir at ambient temperature for about 19 hours. The resulting suspension was filtered though celite and the solvent was removed under reduced pressure. The resulting crude product was purified by reverse chromatography (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% acetonitrile/0.1 M aqueous ammonium acetate −100% acetonitrile over 20 min, 100% acetonitrile hold 5 minutes, 21 mL/min) to afford N4-(3-amino-propyl)-N4-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-pyrimidine-2,4-diamine (0.021 g, 17% yield) as a green solid. RP-HPLC (Table 1, Method e) Rt 1.62 min.; m/z: (M+H)+ 416.1.

Provenance & Evidence