Acetonitrile → HCID 54196047, compound

HRID 569007Notes

Reaction equation

HRID 569007 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[OH:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][CH:15](O)[CH:16]=[CH:17]CC)=[CH:12][CH:11]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].[C:29](#N)C>>[I:8][C:5]1[CH:4]=[N:3][C:2]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:14][CH:15]([CH3:29])[CH:16]=[CH:17][CH2:23][OH:26])=[CH:21][CH:22]=2)=[N:7][CH:6]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 17142232-Chloro-5-iodopyrimidineHCID 86742038HCID 86742038, compound

Product 1

HCID 54196047HCID 54196047, compound

Procedure

A mixture of 1.68 g (7 mmol) of 2-chloro-5-iodopyrimidine, 1.55 g (8 mmol) of (E)-4-(4-hydroxyphenoxy-2-penten-1-ol, 1.24 g (9 mmol) of powdered, anhydrous potassium carbonate and 35 ml of dry acetonitrile was stirred under nitrogen at reflux for a period of 3 hours. The mixture was cooled and filtered, and the filtered solid was thoroughly washed with ether. The filtrates were combined and evaporated to dryness, and the residue partitioned between ether and 1 percent aqueous sodium hydroxide. The aqueous layer was separated and again extracted with ether. The combined organic layers were washed twice with water, dried over MgSO4 and evaporated to dryness. The residual oil was purified by preparative scale HPLC, and then dried in a Kugelrohr apparatus at 55° C. and 0.1 mm Hg for 1 hour. This left 2.75 g (quantitative) of the desired pentenol as a pale yellow, viscous gum.

Workup

  1. temperatureat reflux for a period of 3 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe filtered solid was thoroughly washed with ether
  5. customevaporated to dryness
  6. customthe residue partitioned between ether and 1 percent aqueous sodium hydroxide
  7. customThe aqueous layer was separated
  8. extractionagain extracted with ether
  9. washThe combined organic layers were washed twice with water
  10. dry with materialdried over MgSO4
  11. customevaporated to dryness
  12. customThe residual oil was purified by preparative scale HPLC
  13. customdried in a Kugelrohr apparatus at 55° C.

Sources & evidence

ORD record
ord-33dedf14360a4f28b1825ad6ee848587
Source dataset
uspto-grants-1988_03
Patent number
US04731108

Reaction notes

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