Hydrochloric Acid → HCID 58346439, compound

Participants

Reaction Steps

To a stirred and cooled (0° C.) solution of N-[4-(benzyloxy)-3-chlorophenyl]-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine (1673 mg, 2.7 mmol) in THF (55 mL) was added aq. HCl (2M, 1.6 mL). The resulting clear solution slowly became heterogeneous with a yellow precipitate. The mixture was warmed to rt over a 5 h period, after which time the solvent was removed in vacuo. The crude residue was diluted with EtOAc (5 mL) and aq. Na2CO3 (2M, 100 mL) to attain a pH=11 solution which was vigorously stirred for 1 h. The contents were filtered to a light yellow solid, which was washed with water (400 mL), and then hexanes (500 mL). The collected product was dried under vacuum, to afford the final product (817 mg, 60%) as a light yellow solid. 1H-NMR (DMSO-d6) δ 8.41 (s, 1H), 8.34 (s, 1H), 7.93 (s, 1H), 7.75 (d, 1H), 7.33-7.53 (m, 6H), 7.23 (s, 1H), 5.21 (s, 2H), 4.92 (t, 1H), 4.10 (t, 2H), 3.73 (td, 2H), 3.38 (t, 2H), 2.92 (t, 2H); LCMS RT=3.56 min; [M+H]+=504.2.

Provenance & Evidence