HCID 67313399, compound → HCID 67312776, compound

Participants

Reaction Steps

To a solution of 2-allyl-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine trifluoroacetate (25.0 mg, 0.05 mmol) in ethyl acetate (1.50 mL) was added Pd/C (2.0 mg, 10%) under nitrogen. The reaction was stirred at rt under hydrogen atmosphere (balloon, 1 atm) for 4 h. The Pd/C residue was removed by filtering through a pad of celite and pad was washed with EtOAc (2×3 mL). The combined EtOAc layers were dried over sodium sulfate and the solvent was removed in vacuo. The residue was then separated by preparative HPLC to give (N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-2-propyl-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine trifluoroacetate (salt) (3.4 mg, 15%) as a yellow solid. 1H NMR (CD3CN) δ 8.33 (s, 1H), 7.82 (d, J=2.6 Hz, 1H), 7.65 (s, 1H), 7.49 (dd, J=2.3, 8.9 Hz, 1H), 7.45 (m, 1H), 7.33 (t, 1H), 7.28 (d, J=10 Hz, 1H), 7.14 (d, J=9 Hz, 1H), 7.12 (dt, 1H), 5.23 (s, 2H), 4.08 (t, 2H), 3.40 (t, 2H), 3.04 (t, 2H), 1.88 (m, 2H), 0.94 (t, 3H); LCMS RT=3.91 min, [M+H]+=520.1.

Provenance & Evidence