Ethylene Glycol → 2-[(2-Chloropyrimidin-4-yl)oxy]ethanol

HRID 595153Notes

Reaction equation

HRID 595153 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([OH:10])[CH2:8][OH:9].[Cl:11][C:12]1[N:17]=[C:16](S(C)(=O)=O)[CH:15]=[CH:14][N:13]=1>CN(C=O)C.CCOC(C)=O>[Cl:11][C:12]1[N:17]=[C:16]([O:9][CH2:8][CH2:7][OH:10])[CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 197713792-Chloro-4-(methanesulfonyl)pyrimidine

Product 1

HCID 597640682-[(2-Chloropyrimidin-4-yl)oxy]ethanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.89 g, 6.45 mmol) was added at room temperature to an oven-dried, nitrogen cooled flask containing a suspension of ethylene glycol (1.3 mL, 23.4 mmol) in DMF (29 mL) and the mixture was then stirred for 15 minutes. 2-Chloro-4-(methylsulfonyl)pyrimidine (1.13 g, 5.86 mmol) was then added. The solution was stirred for 1.5 h at room temperature, then diluted with EtOAc (30 mL) and washed with 1:1 water:brine (3×50 mL). The organic extracts were dried over sodium sulfate, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes) to afford 2-[(2-chloropyrimidin-4-yl)oxy]ethanol as a pale yellow solid. MS ESI calcd. for C6H8ClN2O2 [M+H]+ 175. found 175.

Workup

  1. additioncontaining
  2. stirringThe solution was stirred for 1.5 h at room temperature
  3. washwashed with 1:1 water
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c8439823184e438aa5a5fb0733475acc
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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