Reaktion #556545

Reaktionsgleichung

sodium hydride

4,6-diiodopyrimidine

8-methyl-2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde

1,3-dimethylimidazolium chloride

→

(6-iodo-pyrimidin-4-yl)-(8-methyl-2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 4 h
2. 2
   Extraktionextracted with EtOAc
3. 3
   SonstigeThe organic phase was dried on sodium sulphate
4. 4
   Sonstigeevaporated down i
5. 5
   Sonstigeand the residue was purified by preparative HPLC-MS
6. 6
   workup.ADDITIONThe fractions containing the product
7. 7
   Sonstigethe organic solvent was evaporated down i
8. 8
   Sonstigethe grease precipitated
9. 9
   Extraktionwas extracted with EtOAc
10. 10
    SonstigeThe organic phase was dried on sodium sulphate
11. 11
    Filtrationfiltered
12. 12
    Sonstigeevaporated down
13. 13
    Sonstigedried i

Vorschrift

0.131 g (3.00 mmol) sodium hydride (55%, suspension in mineral oil) were added to 0.677 g (2.00 mmol) 4,6-diiodopyrimidine, 0.535 g (3.00 mmol) 8-methyl-2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde (US2005/256099) and 0.133 g (1.00 mmol) 1,3-dimethylimidazolium chloride in 10 mL THF and the mixture was refluxed for 4 h. Then the reaction mixture was mixed with ice water and extracted with EtOAc. The organic phase was dried on sodium sulphate, evaporated down i. vac. and the residue was purified by preparative HPLC-MS. The fractions containing the product were combined and the organic solvent was evaporated down i. vac. The residue was made alkaline with 1N aqueous sodium hydroxide solution and the grease precipitated was extracted with EtOAc. The organic phase was dried on sodium sulphate, filtered, evaporated down and dried i. vac.

Quelle