Sodium Bicarbonate → HCID 22020918, compound

HRID 1793332Notes

Reaction equation

HRID 1793332 reaction equation
Br[CH:2]([CH2:12][Br:13])[CH2:3][O:4][C:5]1[C:6](=[O:11])[NH:7][CH:8]=[N:9][CH:10]=1.C([O-])(O)=O.[Na+]>C(O)C>[Br:13][CH2:12][CH:2]1[O:11][C:6]2[N:7]=[CH:8][N:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22020972HCID 22020972, compound

Product 1

HCID 22020918HCID 22020918, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate (50) (0.0091 mol) and NaHCO3 (0.0113 mol) in ethanol (100 ml) was stirred and refluxed for 16 hours. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated. The residue was taken up in water and ethyl acetate. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: hexane/ethyl acetate 66/33;50/50). The desired fractions were collected and the solvent was evaporated, yielding 1.1 g of 7-(bromomethyl)-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine (intermediate 51).

Workup

  1. temperaturerefluxed for 16 hours
  2. customthe solvent was evaporated
  3. customThe separated organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by short open column chromatography over silica gel (eluent: hexane/ethyl acetate 66/33;50/50)
  7. customThe desired fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-40f74aa4c754468cb801ca900ccfeaa9
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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