Sodium hydride → HCID 19050644, compound

HRID 863763Notes

Reaction equation

HRID 863763 reaction equation
[H-].[Na+].[C:3]([CH:5]1[C:14]2[C:9](=[C:10]([Cl:16])[CH:11]=[CH:12][C:13]=2[Cl:15])[C:7](=[O:8])[O:6]1)#[N:4].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1>>[C:3]([C:5]1([C:21]2[N:22]=[C:23]([O:25][CH3:26])[CH:24]=[C:19]([O:18][CH3:17])[N:20]=2)[C:14]2[C:9](=[C:10]([Cl:16])[CH:11]=[CH:12][C:13]=2[Cl:15])[C:7](=[O:8])[O:6]1)#[N:4]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 19050651HCID 19050651, compound

Product 1

HCID 19050644HCID 19050644, compoundYield 18.5%

Procedure

21.5 g of NaH in oil dispersion are added to 112.75 g of 3-cyano-4,7-dichlorophthalide and 96.7 g of 4,6-dimethoxy-2-methylsulfonyl-pyrimidine. (The hydride is washed with hexane, the hexane removed by suction and the residue covered with DMF and cooled it an ice bath.) The reaction mixture is left to stir overnight at RT and the solution then poured into 3 L of water containing 15 ml of conc. H2SO4 and stirred mechanically until a viscous gum formed around the stirred blade. The water layer is decanted and extracted with 3×400 ml of toluene, the first two extracts added to the gum and the mixture stirred until the gum dissolved. The toluene solution is washed 2×100 ml of water and 1×100 ml of toluene and the combined toluene layers dried over Na2SO4 concentrated to 400 ml and left to stand overnight. The still homogeneous solution is flash-chromatographed over silica gel with toluene (250 ml fraction 5) fractions 5-9 are combined and stripped to give 30 g of the title product m.p. 123°-126° C.

Workup

  1. wash(The hydride is washed with hexane
  2. customthe hexane removed by suction
  3. temperaturecooled it an ice bath
  4. wait) The reaction mixture is left
  5. additionthe solution then poured into 3 L of water containing 15 ml of conc. H2SO4
  6. stirringstirred mechanically until a viscous gum
  7. customformed around the stirred blade
  8. customThe water layer is decanted
  9. extractionextracted with 3×400 ml of toluene
  10. additionthe first two extracts added to the gum
  11. stirringthe mixture stirred until the gum
  12. dissolutiondissolved
  13. washThe toluene solution is washed 2×100 ml of water and 1×100 ml of toluene
  14. dry with materialthe combined toluene layers dried over Na2SO4
  15. concentrationconcentrated to 400 ml
  16. waitleft
  17. waitto stand overnight
  18. customThe still homogeneous solution is flash-chromatographed over silica gel with toluene (250 ml fraction 5) fractions 5-9

Sources & evidence

ORD record
ord-b25ad120da5d4c4e8aa221430dbfb9f1
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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