Aniline → HCID 18009134, compound

Participants

Reaction Steps

To a solution of 4-[4-(2,3-epoxypropoxy)anilino]-6-(2,4-difluoroanilino)pyrimidine (prepared by an analogous procedure to Reference Examples 9 and using the appropriate aniline) (1.4 g) in DMF (11 ml) at 0° C. was added sodium tert-butoxide (580 mg) and the mixture stirred for 10 minutes. To a portion of this solution (2.2 ml) was added 1-bromo-2-fluoroethane (0.11 ml) and the reaction stirred for 1 hour. The solution was then poured into water and extracted with EtOAc. The organic extract was dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with DCM:MeOH; 125:2 to give the product (237 mg, 75%) as a colourless oil. NMR: 2.65 (2H, m), 2.81 (2H, m), 3.79 (1H, dd), 4.01-4.18 (2H, m), 4.51 (2H, t), 4.67 (2H, t), 5.40 (1H, s), 6.82 (2H, d), 7.21 (1H, m), 7.30-7.59 (4H, m), 8.20 (1H, s), 8.84 (1H, s).

Provenance & Evidence