تفاعل #6926

معادلة التفاعل

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

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

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product

المردود 52.0%

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

المردود 52.0%

المذيبات

HCl

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool
2. 2
   ترشيحThe reaction was filtered
3. 3
   غسيلthe 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
   أخرىThe dioxane was removed under vacuum
6. 6
   workup.ADDITIONthe reaction diluted with water
7. 7
   أخرىthe solid which precipitated
8. 8
   ترشيحwas collected by filtration
9. 9
   غسيلwashed with water, iso-hexane and acetone
10. 10
    أخرىby partitioning into a mixture of triethylamine, ethyl acetate and water
11. 11
    غسيلThe organic phase was washed with water
12. 12
    تجفيفdried (magnesium sulphate)
13. 13
    أخرىthe solvent removed under vacuum
14. 14
    أخرىThe residue was triturated with iso-hexane/ethyl acetate

الإجراء التجريبي

(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.

المصدر