Trifluoroacetic acid → N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine

Participants

Reaction Steps

{5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-yl}-carbamic acid tert-butyl ester 11 (0.33 mmol) is dissolved in DCM (2 mL) and treated with TFA (3 mL). The reaction mix is stirred at rt for 2 h. The solvent is removed to afford an off white solid residue. The residue is taken in water, the pH neutralized with 5% Na2CO3 and extracted with DCM:IPA=3:1 (3×40 mL). The organic layer is washed with brine and dried over Na2SO4. Evaporation of the organic solvent under reduced pressure affords N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine 12, which is used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 10.37 (s, 1H), 8.90 (s, 2H), 8.47 (bs, 1H), 7.79 (bs, 1H), 7.71-7.69 (m, 2H), 7.08-7.06 (m, 2H), 6.36 (bs, 2H), 3.81 (s, 3H), 2.43 (s, 3H). MS (m/z) (M+1)+: 308.2.

Provenance & Evidence