反应详情

Under an atmosphere of argon, 9-BBN (0.348 ml of a 0.5 molar solution in hexane, 0.174 mmol) was added to a solution of 4-amino-6-(2,4-dichloro-phenyl)-2-phenyl-pyrimidine-5-carbonitrile (60 mg, 0.174 mmol) in THF (1 ml) and stirred for 2.5 h at r.t. Potassium-tert-butylate (20 mg, 0.174 mmol) was added, followed by a drop of Methyl iodide after 10 min. The mixture was stirred overnight, then ethanolamine (11 mg, 0.174 mmol) was added and the mixture was heated to 50° C. for 3 h. After cooling, the mixture was filtered, and the filtrate was evaporated. Purification of the re-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5–95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min) gave the tide compound, MS: m/e=358.9 (M+H+), (12 mg, 19%) as a foam.

1. stirringThe mixture was stirred overnight
2. temperaturethe mixture was heated to 50° C. for 3 h
3. temperatureAfter cooling
4. filtrationthe mixture was filtered
5. customthe filtrate was evaporated
6. customPurification of the
7. dissolutionre-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5–95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min)
8. customgave the tide compound, MS