반응 #6926

반응 방정식

(4-Benzyloxyphenyl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine

5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan

→

product

수율 52.0%

5-(4-(4-Benzyloxy-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl)-furan-2-carbaldehyde

수율 52.0%

용매

HCl

반응 조건

후처리

1. 1
   온도to cool
2. 2
   여과The reaction was filtered
3. 3
   세척the residue washed with dioxane (20 ml) and 2N HCl (20 ml)
4. 4
   workup.STIRRINGThe combined filtrate and washings were stirred at room temperature for a further hour
5. 5
   기타The dioxane was removed under vacuum
6. 6
   workup.ADDITIONthe reaction diluted with water
7. 7
   기타the solid which precipitated
8. 8
   여과was collected by filtration
9. 9
   세척washed with water, iso-hexane and acetone
10. 10
    기타by partitioning into a mixture of triethylamine, ethyl acetate and water
11. 11
    세척The organic phase was washed with water
12. 12
    건조dried (magnesium sulphate)
13. 13
    기타the solvent removed under vacuum
14. 14
    기타The residue was triturated with iso-hexane/ethyl acetate

실험 절차

(4-Benzyloxyphenyl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (4.0 g, 11.0 mmol), 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan (J. Chem. Soc., Chem. Commun., (1988), 560) (6.0 g, 14.0 mmol) were reacted together in a procedure analogous to Procedure B above for 20 hrs. The reaction mixture was allowed to cool, 1N HCl (50 ml) added and stirred at room temperature for 15 minutes. The reaction was filtered and the residue washed with dioxane (20 ml) and 2N HCl (20 ml). The combined filtrate and washings were stirred at room temperature for a further hour. The dioxane was removed under vacuum, the reaction diluted with water and the solid which precipitated was collected by filtration, and washed with water, iso-hexane and acetone. This precipitate was converted to the free base by partitioning into a mixture of triethylamine, ethyl acetate and water. The organic phase was washed with water, dried (magnesium sulphate) and the solvent removed under vacuum. The residue was triturated with iso-hexane/ethyl acetate to give the product (2.41 g, 52%) as a yellow solid; δH [2H6]-DMSO 10.60 (1H, b, NH), 9.83 (1H, s, CHO), 9.30 (1H, s, 2-H), 9.08 (1H, s, 5-H or 8-H), 8.76 (1H, s, 5-H or 8-H), 7.89 (1H, d, furan-H), 7.82 (2H, d, 2′-H, 6′-H), 7.65–7.42 (6H, m, 5×Ph-H, furan-H), 7.21 (2H, d, 3′-H, 5′-H), 5.26 (2H, s, OCH2); m/z (M+1)+423.

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