Tetrahydrofuran → HCID 68706988, compound

HRID 638892Notes

Reaction equation

HRID 638892 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[C:17]2[CH2:18][CH2:19][CH2:20][C:16]=2[N:15]=[C:14]([NH2:21])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:23][C:24](=O)[C:25]([O-:27])=[O:26].[CH2:29]1COC[CH2:30]1>C(O)C>[CH2:29]([O:27][C:25]([C:24]1[N:21]=[C:14]2[N:15]([C:16]3[CH2:20][CH2:19][CH2:18][C:17]=3[C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:13]2)[CH:23]=1)=[O:26])[CH3:30]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 6994776Propanoic acid, 3-bromo-2-oxo-, ion(1-)HCID 22224522HCID 22224522, compound

Product 1

HCID 68706988HCID 68706988, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

6.0 gram (21 mmol) of 4-benzyloxyethoxy-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamine was dissolved in 100 ml dry THF. Bromopyruvate (8 ml) was then added dropwise with in five minutes. The mixture was stirred at 23° C. for one hour. It was then filtered and washed with ether to give a solid. This solid was then dissolved in 50 ml ethanol and refluxed for two hours. The reaction mixture was cooled to room temperature and partitioned between 350 ml chloroform and 200 ml saturated sodium bicarbonate. The organic layer was separated and dried over magnesium sulfate. Filter off the drying agent and concentrate to give 5.36 gram of product (67% Yield). (M+H) 382.1

Workup

  1. filtrationIt was then filtered
  2. washwashed with ether
  3. customto give a solid
  4. temperaturerefluxed for two hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. custompartitioned between 350 ml chloroform and 200 ml saturated sodium bicarbonate
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. filtrationFilter off the drying agent
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-0679a01b5ccb41e28099b2d1f0f0932d
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

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