Methanol → HCID 86630692, compound

HRID 1851218Notes

Reaction equation

HRID 1851218 reaction equation
[Br:1][C:2]1[N:18]=[C:5]2[N:6]=[C:7]([Cl:17])[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9](Br)[N:4]2[N:3]=1.CO.C1COCC1>C(O)(=O)C>[Br:1][C:2]1[N:18]=[C:5]2[N:6]=[C:7]([Cl:17])[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 86630693HCID 86630693, compound

Product 1

HCID 86630692HCID 86630692, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 29.4 g 2,7-dibromo-5-chloro-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine, 125 mL methanol, 500 mL THF, 12.9 mL glacial acetic acid and 14.7 g of Zn/Cu pair were stirred at 45° C. After 3 and 5 hours additional portions of 7.3 g Zn/Cu pair were added. The mixture was filtered through celite and the filtrate was diluted with water and ethyl acetate. The phases were separated and the water layer was extracted with ethyl acetate. The combined organic layers were washed with saturated Na2CO3 solution, dried over Na2SO4 and the solvent was evaporated. The solid residue was stirred in a mixture of 2-propanol/ethanol (3:1) for 2 h. The crude product was filtered and dried and was used without further purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. additionthe filtrate was diluted with water and ethyl acetate
  3. customThe phases were separated
  4. extractionthe water layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated Na2CO3 solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent was evaporated
  8. stirringThe solid residue was stirred in a mixture of 2-propanol/ethanol (3:1) for 2 h
  9. filtrationThe crude product was filtered
  10. customdried
  11. customwas used without further purification

Sources & evidence

ORD record
ord-11aaaa22288d4a2086668d3b609189d9
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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