Sodium hydride → HCID 21333231, compound

HRID 1390666Notes

Reaction equation

HRID 1390666 reaction equation
C([N:8]1[CH2:12][CH:11]([CH2:13][OH:14])[O:10][CH:9]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.[H-].[Na+].Cl[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1>C(COC)OC>[CH2:9]([NH:8][CH2:12][CH:11]([OH:10])[CH2:13][O:14][C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 43596504N-003

Product 1

HCID 21333231HCID 21333231, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of 26.93 g of 3-benzyl-5-hydroxymethyl-2-phenyl-oxazolidine in 100 ml of dimethoxyethane is added dropwise to a suspension of 2.4 g of sodium hydride in 50 ml of dimethoxyethane, whilst keeping the temperature of the reaction mixing at 20° C. The mixture is then stirred for 7 hours, after which a solution of 11.45 g of 2-chloro-pyrimidine in 30 ml of dimethoxyethane is added dropwise at 20° C. After stirring for 20 hours and boiling under reflux, the solvent is distilled off under reduced pressure, the residue is warmed with 10 ml of concentrated hydrochloric acid and 30 ml of water to 60° C. and then cooled, and the mixture is extracted with ether. 15 ml of 10 N sodium hydroxide solution are added to the aqueous phase at 0° C., the mixture is then extracted with ethyl acetate and the organic phase is dried over sodium sulphate, filtered and evaporated in vacuo. The residue is dissolved in acetone and a solution of 9.0 g of oxalic acid in acetone is added. The hydrogen-oxalate of 1-benzylamino-3-(2-pyrimidinyloxy)-2-propanol, of melting point 188°-189° C., is obtained. From this, the free base is obtained as an oil by adding sodium hydroxide solution at 0° C., extracting with ethyl acetate, drying the organic phase over sodium sulphate, filtering and evaporating.

Workup

  1. additionmixing at 20° C
  2. stirringAfter stirring for 20 hours
  3. temperatureunder reflux
  4. distillationthe solvent is distilled off under reduced pressure
  5. temperaturecooled
  6. extractionthe mixture is extracted with ether
  7. addition15 ml of 10 N sodium hydroxide solution are added to the aqueous phase at 0° C.
  8. extractionthe mixture is then extracted with ethyl acetate
  9. dry with materialthe organic phase is dried over sodium sulphate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. dissolutionThe residue is dissolved in acetone
  13. additiona solution of 9.0 g of oxalic acid in acetone is added

Sources & evidence

ORD record
ord-45e9bfb148b74eb5a4a5cf6afa20e923
Source dataset
uspto-grants-1979_02
Patent number
US04139623

Reaction notes

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