p-Toluenesulfonic acid → HCID 71577744, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of impure 6-amino-5-methoxy-2-methylisoindolin-1-one (<0.57 mmol), 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (66 mg, 0.31 mmol) and pTSA (59 mg, 0.31 mmol) in dioxane (4 mL) was heated to 100° C. for 4 h. DCM (10 mL) and saturated aqueous NaHCO3 (10 mL) were added and the organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via reversed phase preparative HPLC gave 5-methoxy-2-methyl-6-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)isoindolin-1-one (15 mg, 13%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=368 at 2.89 min. 1H NMR (400 MHz, CDCl3): δ 9.04 (s, 1H), 8.17 (s, 1H), 7.80 (s, 1H), 6.93 (s, 1H), 5.26 (br s, 1H), 4.31 (s, 2H), 3.97 (s, 3H), 3.20 (d, J 4.7, 3H), 3.18 (s, 3H).

Provenance & Evidence