Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]- → 4-(4-Benzyloxyanilino)-6-(5-formylfuran-2-yl) pyrido[3,4-d]pyrimidine

HRID 585616노트

반응식

HRID 585616 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]3[CH:25]=[C:24](Cl)[N:23]=[CH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:27]1CCO[CH:28]1[C:32]1[O:36][C:35]([Sn](CCCC)(CCCC)CCCC)=[CH:34][CH:33]=1>Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]3[CH:25]=[C:24]([C:35]4[O:36][C:32]([CH:28]=[O:27])=[CH:33][CH:34]=4)[N:23]=[CH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 10960952Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]-HCID 219521684-(4-Benzyloxyanilino)6-chloropyrido[3,4-d]pyrimidine

생성물 1

HCID 219520464-(4-Benzyloxyanilino)-6-(5-formylfuran-2-yl) pyrido[3,4-d]pyrimidine수율 52%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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-hexanelethyl 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.

후처리

  1. temperatureto cool
  2. filtrationThe reaction was filtered
  3. washthe residue washed with dioxane (20 ml) and 2N HCl (20 ml)
  4. stirringThe combined filtrate and washings were stirred at room temperature for a further hour
  5. customThe dioxane was removed under vacuum
  6. additionthe reaction diluted with water
  7. customthe solid which precipitated
  8. filtrationwas collected by filtration
  9. washwashed with water, iso-hexane and acetone
  10. customby partitioning into a mixture of triethylamine, ethyl acetate and water
  11. washThe organic phase was washed with water
  12. dry with materialdried (magnesium sulphate)
  13. customthe solvent removed under vacuum
  14. customThe residue was triturated with iso-hexanelethyl acetate

출처 및 근거

ORD 기록
ord-0c512f7d38674b23b17d0d03f5ee4b72
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933299B1

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