反応 #6926

反応方程式

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

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

→

product

収率 52.0%

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

収率 52.0%

溶媒

HCl

反応条件

後処理

1. 1
   温度to cool
2. 2
   ろ過The reaction was filtered
3. 3
   洗浄the 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
   その他The dioxane was removed under vacuum
6. 6
   workup.ADDITIONthe reaction diluted with water
7. 7
   その他the solid which precipitated
8. 8
   ろ過was collected by filtration
9. 9
   洗浄washed with water, iso-hexane and acetone
10. 10
    その他by partitioning into a mixture of triethylamine, ethyl acetate and water
11. 11
    洗浄The organic phase was washed with water
12. 12
    乾燥dried (magnesium sulphate)
13. 13
    その他the solvent removed under vacuum
14. 14
    その他The residue was triturated with iso-hexane/ethyl acetate

実験手順

(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.

出典