Реакция #727151

Уравнение реакции

sodium hydride

ethylene glycol

7-fluoroquinazolin-4-ol

→

7-(2-hydroxyethoxy)quinazolin-4-ol

Выход 45.1%

Растворители

dimethylacetamide

Условия реакции

Обработка

1. 1
   Температураwere cooled in an ice-bath under a nitrogen atmosphere
2. 2
   ТемператураThe reaction mixture was heated to 110° C. for 16 hours
3. 3
   Концентрированиеthe mixture was concentrated to approximately half volume
4. 4
   workup.ADDITIONThe mixture was poured into water
5. 5
   ФильтрацияThe resultant precipitate was filtered
6. 6
   Другоеdried in a vacuum oven at 65° C. for 16 hours
7. 7
   ДругоеThe residue was triturated with diethyl ether

Методика

A mixture of sodium hydride (60% in oil, 7.67 g, 189.6 mmol) and dimethylacetamide (160 ml) were cooled in an ice-bath under a nitrogen atmosphere and then ethylene glycol (18.2 g, 284 mmol) was slowly added. The reaction mixture was warmed to 60° C. for 10 minutes and then 7-fluoroquinazolin-4-ol (7.75 g, 47.3 mmol) was slowly added. The reaction mixture was heated to 110° C. for 16 hours and then the mixture was concentrated to approximately half volume. The mixture was poured into water and the pH of the solution was adjusted to 5 with dilute hydrochloric acid. The resultant precipitate was filtered and then dried in a vacuum oven at 65° C. for 16 hours. The residue was triturated with diethyl ether to give 7-(2-hydroxyethoxy)quinazolin-4-ol (4.4 g) as an off white solid which was used in subsequent steps without further purification: MS (+ve ESI): 207 (M+H)+ MS (−ve ESI): 205 (M−H)−.

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