Hydrochloric Acid → HCID 18186493, compound

Participants

Reaction Conditions

Reaction Steps

4-Anilino-5-(ethoxymethyl)-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine (Example 86, 100 mg, 0.23 mmol) was dissolved in NMP (2 ml). 3-Hydroxy-5-methylisoxazole (45 mg, 0.46 mmol) and ethereal hydrogen chloride (1.0M; 0.46 ml, 0.46 mmol) were added, and the solution was heated at 100° C. for 20 hours. Volatile material was removed by evaporation, and the residue was dissolved in 10% methanol solution in DCM (3 ml) and loaded on a Varian Mega Bond Elut column. The column was eluted with 0-2.5% methanol solution in DCM containing 0.5% aqueous ammonia solution. Concentration of the appropriate fractions and trituration of the residue with diethyl ether gave the product as a white crystalline solid (49 mg, 44%). NMR: 2.17 (s, 6H), 2.22 (s, 3H), 2.2-2.45 (m, 2H), 3.75-3.9 (m, 3H), 4.73 (br s, 1H), 4.49 (s, 2H), 5.78 (s, 1H), 6.80 (d, 2H), 7.02 (t, 1H), 7.30 (dd, 2H), 7.50 (d, 2H), 7.70 (d, 2H) 8.04 (s, 1H), 8.76 (s, 1H), 9.05 (s, 1H); MS (MH+): 491.5.

Provenance & Evidence