Ethyl Glycolate → HCID 70982233, compound

HRID 2175272Notes

Reaction equation

HRID 2175272 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br:10][C:11]1[CH:12]=[N:13][C:14](Cl)=[N:15][CH:16]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:10][C:11]1[CH:12]=[N:13][C:14]([O:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:15][CH:16]=1

Participants

6

Reactant 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 70982233HCID 70982233, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-hydroxyacetate (0.081 g, 0.775 mmol) in toluene (1.0 mL) was added NaH (60% in mineral oil, 0.037 g, 0.931 mmol) at room temperature. The mixture was stirred for 30 min and a solution of 5-bromo-2-chloropyrimidine (0.100 g, 0.517 mmol) in toluene (0.5 mL) was added. The reaction mixture was stirred at 60° C. for 16 h. The mixture was diluted with EtOAc and slowly quenched with water. The organic layer was separated, washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (82 mg, 61% yield) as a clear colorless oil. LCMS, [M+H]+=260.9.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 16 h
  2. customslowly quenched with water
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide the crude material
  9. customThe crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-1b1b0321264f4f20b693213dc0e2a689
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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