Sodium hydride → HCID 22224522, compound

HRID 1744972Notes

Reaction equation

HRID 1744972 reaction equation
[H-].[Na+].C1COCC1.[CH2:8]([O:15][CH2:16][CH2:17][OH:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[C:20]1[C:25]2[CH2:26][CH2:27][CH2:28][C:24]=2[N:23]=[C:22]([NH2:29])[N:21]=1>C1COCC1>[CH2:8]([O:15][CH2:16][CH2:17][O:18][C:20]1[C:25]2[CH2:26][CH2:27][CH2:28][C:24]=2[N:23]=[C:22]([NH2:29])[N:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2303324-chloro-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-amineHCID 86604210HCID 86604210, compound

Product 1

HCID 22224522HCID 22224522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S M:Ross, L. O.; Goodman, L.; Baker, B. R. J. Am. Chem. Soc. 1959, 81, 3108) To stirred suspension of NaH (60% 552 mg) in THF 2-benzyloxyethanol (3.38 g, 20 mmol) was slowly added at room temperature. After the addition, 3.28 grams (19.4 mmol) of 4-chloro-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamine was dissolved in 200 ml THF and added to it and the mixture was refluxed for 3 hours. Then the solvent was removed in vacuo and 100 ml water was added to the residue. The product was extracted with chloroform; washed well with water and dried over anhydrous MgSO4. It was filtered and concentrated. Low melting solid; Yield: 4.2 gram (73%); (M+H) 286.1

Workup

  1. additionwas slowly added at room temperature
  2. additionadded to it
  3. temperaturethe mixture was refluxed for 3 hours
  4. customThen the solvent was removed in vacuo and 100 ml water
  5. additionwas added to the residue
  6. extractionThe product was extracted with chloroform
  7. washwashed well with water
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationIt was filtered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-989e2f72d2cd4080a5fa14c748cc6b8f
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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