Ethylene Glycol → HCID 69059589, compound

Participants

Reaction Conditions

Reaction Steps

Ethylene glycol (150 ml) was treated with sodium hydride (60% in oil, 3.15 g) and the exotherm controlled to about 10° C. with an ice-bath. N-[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-fluoroquinazolin-4-amine (obtained as described in Example 1, preparation of starting materials, 12 g) was added in small portions and the mixture heated at 120° C. for 1 hour. The slurry was cooled, poured into water/saturated ammonium chloride (1.5 litres) and the solid collected and dried to give 2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethanol (12.6 g, 95%); NMR spectrum (DMSO-d6) 3.89-3.98 (m, 2H), 4.33 (t, 2H), 5.27 (s, 2H), 5.37 (t, 1H), 7.13 (d, 1H), 7.23 (d, 1H), 7.31-7.38 (m, 2H), 7.57 (d, 1H), 7.68-7.75 (m, 2H), 7.83-7.90 (m, 1H), 8.26 (d, 1H), 8.54 (s, 1H), 8.58 (d, 1H), 10.41 (s, 11H); Mass spectrum MH+ 422.

Provenance & Evidence