Potassium Carbonate → HCID 54446419, compound

HRID 1155042Notes

Reaction equation

HRID 1155042 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:11]3[O:23][C@H:22]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[N:9]=[CH:10][C:3]=12.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[CH:36]=[CH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C)C=O>[CH2:35]([S:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:11]3[O:23][C@H:22]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[N:9]=[CH:10][C:3]=12)[CH:36]=[CH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98116BromomethylstyreneHCID 178476365HCID 178476365, compound

Product 1

HCID 54446419HCID 54446419, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-mercapto-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidine (1.0 g) and potassium carbonate (0.37 g) in N,N-dimethylformamide was stirred for 10 minutes and then cinnamyl bromide (0.53 g) was added. After stirring for 3 hr. at 40° C. the solution was filtered and 100 ml chloroform was added. The solution was extracted with water. The chloroform layer was dried, filtered and taken to dryness on a rotary evaporator. The residue was purified on a column of silica gel using chloroform as the eluant. The fractions containing the product were pooled and taken to dryness in vacuo. The residue was dissolved in chloroform, filtered through a Millipore filter in vacuo and evaporated in vacuo, to give the product 4-cinnamylthio-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidine as a glass.

Workup

  1. stirringAfter stirring for 3 hr
  2. filtrationat 40° C. the solution was filtered
  3. addition100 ml chloroform was added
  4. extractionThe solution was extracted with water
  5. dry with materialThe chloroform layer was dried
  6. filtrationfiltered
  7. customtaken to dryness on a rotary evaporator
  8. customThe residue was purified on a column of silica gel
  9. additionThe fractions containing the product
  10. dissolutionThe residue was dissolved in chloroform
  11. filtrationfiltered through a Millipore
  12. filtrationfilter in vacuo
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-9551b02af93f414d8e17541a82646f89
Source dataset
uspto-grants-1981_11
Patent number
US04299824

Reaction notes

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