1-Propanol, 3-amino-2,2-dimethyl- → 3-{4-[2-(4-Fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2,2-dimethylpropan-1-ol

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask charged with 2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-8-methoxymethylimidazo[1,2-a]pyrazine (˜2-3% impurity within 3.05 g, 7.95 mmol of 2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-8-methylimidazo[1,2-a]pyrazine) was dissolved in ACN (70 mL) to which was added 3-amino-2,2-dimethyl-propan-1-ol (Lancaster, 4.1 g, 96.8 mmol) at ambient temperature followed by heating to about 80° C. for about 3 h. After this time the reaction was cooled to ambient temperature and purified in 200-300 mg batches using RP-HPLC (Table 1, Method i). The pure fractions were combined and concentrated to remove the organic solvent. The resulting precipitate was filtered from the aqueous layer and dried in a vacuum overnight to give the title compound as a white solid (0.054 g, 1.5% yield). LC/MS (Table 1, Method b) Rt=1.77 min; MS m/z: 414.0 (M+H)+.

Provenance & Evidence