Potassium Carbonate → HCID 10430232, compound

HRID 507822Notes

Reaction equation

HRID 507822 reaction equation
[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:8]=[N:7][C:6]=2[NH:5][C:4]1=[O:22])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:29]([O:32][CH2:33][CH2:34]Br)(=[O:31])[CH3:30]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:29]([O:32][CH2:33][CH2:34][N:5]1[C:6]2[N:7]=[CH:8][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:10]=2[C:11](=[O:12])[N:3]([CH2:1][CH3:2])[C:4]1=[O:22])(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 100657321-ethyl-3,7-dihydro-7-[(4-methoxyphenyl)methyl]-1H-Purine-2,6-dione

Product 1

HCID 10430232HCID 10430232, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

Acetonitrile was added to a mixture of Compound 5A (about 1.0 mole), anhydrous potassium carbonate (about 1.5 moles) and tetrabutylammonium hydrogen sulfate (about 0.05 mole). 2-bromoethyl acetate (about 1.5 moles) was added in three separate portions (0.72 mole in the beginning, another 0.45 mole after about 2 hours of reaction, and then the remaining 0.33 mole after about another 1 hour of reaction) during the course of the reaction at about 80-85° C. The total reaction time was about 7 hours. The reaction mixture was cooled to about room temperature and filtered. The filtrate was concentrated. Aqueous isopropanol was added to crystallize the product. The product was filtered, washed with aqueous isopropanol, and dried to provide Compound 6A in about a 75-80% yield.

Workup

  1. customseparate portions (0.72 mole in the beginning
  2. customanother 0.45 mole after about 2 hours of reaction
  3. customthe remaining 0.33 mole after about another 1 hour of reaction)
  4. customduring the course of the reaction at about 80-85° C
  5. temperatureThe reaction mixture was cooled to about room temperature
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. additionAqueous isopropanol was added
  9. customto crystallize the product
  10. filtrationThe product was filtered
  11. washwashed with aqueous isopropanol
  12. customdried

Sources & evidence

ORD record
ord-e0a2568340c6469282b28d613c10dcef
Source dataset
uspto-grants-2010_08
Patent number
US07786301B2

Reaction notes

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