Sodium hydride → HCID 22224522, compound

HRID 638891Notes

Reaction equation

HRID 638891 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

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-eda375d0f051412c9c7bc43b3bd38a60
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

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