Acetic Anhydride → HCID 178424307, compound

HRID 430507Notes

Reaction equation

HRID 430507 reaction equation
[CH3:1][C:2]1[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:4](=[O:11])[C:5]2[N:10]=[N:9][NH:8][C:6]=2[N:7]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]=O.C(OC(=O)C)(=O)C>O1CCOCC1>[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]=[CH:1][C:2]1[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:4](=[O:11])[C:5]2[N:10]=[N:9][NH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 142732-PyridinecarboxaldehydeHCID 178424316HCID 178424316, compound

Product 1

HCID 178424307HCID 178424307, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of fused zinc chloride (0.551 g, 4.04 mmol) and dioxane (20 mL) was added 5-methyl-6-o-tolyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one (0.488 g, 2.02 mmol),2-pyridinecarboxaldehyde (0.58 mL, 6.06 mmol), and acetic anhydride (0.57 mL, 6.06 mmol). The mixture was heated to 70° C. for 6 hours, cooled, and quenched with saturated sodium bicarbonate. This mixture was stirred overnight at ambient temperature. The dioxane was removed at reduced pressure and the resulting black liquid was extracted with methylene chloride. The organic phase was dried over magnesium sulfate, treated with activated carbon, filtered, and concentrated. The residue (1.5 g) was flash chromatographed on silica gel (50 g). Elution with 50% and 60% ethyl acetate/hexane gave 5-(2-pyridin-2-yl-vinyl)-6-o-tolyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one (0.023 g, 3.5%).

Workup

  1. temperaturecooled
  2. customquenched with saturated sodium bicarbonate
  3. customThe dioxane was removed at reduced pressure
  4. extractionthe resulting black liquid was extracted with methylene chloride
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. additiontreated with activated carbon
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel (50 g)
  10. washElution with 50% and 60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-861ee840909d462fa825359e44bfc24e
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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