Trifluoroacetic acid → Ammonia methanol

Participants

Reaction Conditions

Reaction Steps

A sealed tube charged with enantiomerically pure mono-SNAr product 57a (2.25 g, 8 mmol), aniline 7 (1.80 g, 8.8 mmol), TFA (1.12 mL) and methanol (18 mL) was stirred at 100° C. for 24 hours. The resulting viscous but homogeneous solution was concentrated and the residue was chromatographed (silica gel, CH2Cl2 then 2-5% 2N NH3/MeOH in CH2Cl2) to afford the expected 2,4-diaminopyrimidine derivative 60a (2.28 g, 63%; purity: 95% AUC; enantiomeric purity: greater than 99% as determined by chiral HPLC. The chiral analytical data, 1H NMR and LCMS analyses were found to be identical with the enantiomer designated E1; [α]DRT +44.4° (c 1.0, MeOH).

Provenance & Evidence