Potassium Hydroxide → 1-Cyclopropylmethylcytosine

HRID 328200Notes

Reaction equation

HRID 328200 reaction equation
[OH-].[K+].Br[CH:4]1[CH2:9][N:8]([CH2:10][CH:11]2[CH2:13][CH2:12]2)[C:7](=[O:14])[N:6]=[C:5]1[NH2:15]>CO>[CH:11]1([CH2:10][N:8]2[CH:9]=[CH:4][C:5]([NH2:15])=[N:6][C:7]2=[O:14])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 214443055-Bromo-1-cyclopropylmethyl-5,6-dihydrocytosine

Product 1

HCID 214443201-Cyclopropylmethylcytosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.55 g. of 85% potassium hydroxide in 93 mml. of methanol cooled to 5°, was added 17.0 g. of 5-bromo-1-cyclopropylmethyl-5,6-dihydrocytosine. The mixture was stirred and allowed to warm spontaneously. When the initial reaction, which had warmed the mixture to 30°, subsided, the mixture was refluxed for 5 minutes and allowed to cool and stand at room temperature overnight. The suspension was evaporated under reduced pressure on a water bath at 86°. The residue was triturated was 300 ml. of water on a steam bath and chilled in ice before filtering. The resulting 1-cyclopropylmethylcytosine was washed with cold water and dried in a vacuum desiccator over potassium hydroxide; yield, 9.50 g., m.p. 264°-266°. A sample for analysis was recrystallized from ethanol; m.p. 265°-267°.

Workup

  1. additionwas added 17.0 g
  2. temperatureto warm spontaneously
  3. customWhen the initial reaction, which
  4. temperaturehad warmed the mixture to 30°
  5. temperaturethe mixture was refluxed for 5 minutes
  6. temperatureto cool
  7. customThe suspension was evaporated under reduced pressure on a water bath at 86°
  8. customThe residue was triturated
  9. temperatureof water on a steam bath and chilled in ice
  10. filtrationbefore filtering
  11. washThe resulting 1-cyclopropylmethylcytosine was washed with cold water
  12. dry with materialdried in a vacuum desiccator over potassium hydroxide
  13. customyield
  14. customA sample for analysis was recrystallized from ethanol

Sources & evidence

ORD record
ord-c22d60afe84046718e25281946b69e07
Source dataset
uspto-grants-1977_04
Patent number
US04016267

Reaction notes

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