N,N'-Dimethylethylenediamine → HCID 56932316, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-iodobenzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (50 mg, 0.12 mmol) in dioxane (1 mL) were added morpholin-3-one (15 mg, 1.25 eq), copper iodide (4.4 mg, 0.2 eq), potassium phosphate (49 mg, 2 eq) and N,N′-dimethylethylene diamine (5 μl, 0.4 eq). After stirring for 16 h at 90° C., the reaction mixture was partitioned between 0.5M EDTA and DCM. The aqueous phase was extracted with DCM, the combined organic phases dried over sodium sulfate and evaporated. The residue was purified by preparative HPLC to yield the title compound (23 mg, 56 μmol, 47%). 1H NMR (d6-DMSO) δ 9.85 (s, 1H), 8.92 (s, 1H), 8.06 (s, 2H), 7.56 (s, 1H), 7.43 (s, 1H), 7.39-7.35 (m, 1H), 7.33-7.29 (m, 1H), 7.20-7.13 (m, 1H), 5.57 (s, 2H), 4.17 (s, 2H), 3.96-3.91 (m, 2H), 3.84 (s, 3H), 3.69-3.64 (m, 2H); LC-MS method B, (ES+) 405.1, RT=6.31 min.

Provenance & Evidence