Sodium Methoxide → HCID 178501190, compound

Participants

Reaction Conditions

Reaction Steps

cis-Ethyl 4-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanecarboxylate (0.030 g, 0.057 mmol), sodium methoxide (0.0033 g, 0.063 mmol) and methanol (2 mL) were combined and heated in a resealable Schlenk tube for 48 h at 75° C. Purification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 15.6-16.5 min) afforded cis-methyl 4-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanecarboxylate as a white powder (0.010 g, 0.020 mmol): RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 11.82 min; 1H NMR (DMSO-d6, 400 MHz) δ 10.85 (s, 1H), 8.23 (s, 1H), 7.92 (d, 2H), 7.65 (d, 2H), 7.12 (s, 1H), 6.80 (s, 1H), 4.67 (m, 1H), 3.63 (s, 3H), 3.27 (m, 1H), 2.40 (s, 3H), 2.35 (s, 3H), 2.07 (m, 6H), 1.61 (m, 2H).

Provenance & Evidence