반응 #169014

반응 방정식

Sodium bicarbonate

5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

furan 2-boronic acid

→

5-(5-Furan-2-yl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

수율 15.6%

용매

dioxane

반응 조건

후처리

1. 1
   기타cap pressure flask
2. 2
   온도The reaction mixture was cooled
3. 3
   기타partitioned between water and ethyl acetate
4. 4
   기타The organic phase was separated
5. 5
   건조dried (MgSO4)
6. 6
   여과filtered
7. 7
   기타evaporated under reduced pressure
8. 8
   기타The residue was purified by flash chromatography (3% to 5% MeOH in methylene chloride with 1% ammonium hydroxide)

실험 절차

5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (400 mg, 1 mmol), furan 2-boronic acid (285 mg, 1.5 mmol) and Pd(Ph3)2Cl2 (50 mg) were taken up in 13 mL of degassed dioxane in a screw cap pressure flask. Sodium bicarbonate (2 mL of 2M aqueous solution) was added, and the reaction mixture was heated to 105° C. for 40 hours. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography (3% to 5% MeOH in methylene chloride with 1% ammonium hydroxide) to yield 53 mg of 5-(5-Furan-2-yl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (M+H)=339. Mp=253.7-254.6° C.

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