Water → Methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}(2,2,2-trifluoroethyl)carbamate

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Reaction Conditions

Reaction Steps

3.470 g (8.138 mmol) of the compound from example 31A were suspended in 35 ml of THF, 358 mg (8.952 mmol) of sodium hydride (60% suspension in mineral oil) were added at 0° C. and the mixture was stirred at 0° C. for 90 min, forming a solution. 2.519 g (8.952 mmol) of 2,2,2-trifluoroethyl trichloromethanesulfonate were added and the mixture was stirred at RT for 48 h. The mixture was then stirred with water and concentrated on a rotary evaporator. The residue was taken up in ethyl acetate, and the organic phase was washed twice with water and dried over sodium sulfate. This gave 5.005 g of the target compound (79% of theory, purity by HPLC 65%). 250 mg of residue were purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10).

Provenance & Evidence