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

Participants

Reaction Steps

4-(4-Benzyloxyanilino)-6-chloropyrido[3,4-d]pyrimidine (4.0 g, 110 mmol), 2-(1,3-dioxolan-2-yl)-5-(tributylstannyl)furan (J. Chem. Soc., Chem Commun., (1988), 560) (6.0 g, 14.0 mmol) were reacted together according to Procedure B for 20 hrs. The reaction mixture was allowed to cool, 1N HCl (50 ml) added and stirred at RT 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 RT 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, 5x Ph-H, furan-H), 7.21 (2H, d, 3′-H, 5′-H), 5.26 (2H, s, OCH2); m/z (M+1)+423

Provenance & Evidence