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

HRID 410707Notes

Reaction equation

HRID 410707 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:15][C:16]1[N:21]=[C:20](S(C)(=O)=O)[CH:19]=[CH:18][N:17]=1>O1CCCC1>[Cl:15][C:16]1[N:21]=[C:20]([O:3][CH2:2][CH2:1][OH:4])[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 197713792-Chloro-4-(methanesulfonyl)pyrimidine

Product 1

HCID 597640682-[(2-Chloropyrimidin-4-yl)oxy]ethanolYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethylene glycol (865 μL, 15.5 mmol) in tetrahydrofuran (19 mL) was added sodium bis(trimethylsilyl)amide (2.0 M in tetrahydrofuran, 4.66 mL, 4.7 mmol) at room temperature. The mixture was stirred for 15 minutes, then 2-chloro-4-(methylsulfonyl)pyrimidine (747 mg, 3.88 mmol) was added. The reaction mixture was stirred for 1 h at room temperature, concentrated, then purified by column chromatography on silica gel (Biotage 50 G, eluting with 0:100 to 100:0 ethyl acetate:hexanes) to give 2-[(2-chloropyrimidin-4-yl)oxy]ethanol (416 mg, 2.37 mmol, 61% yield) as a white solid. MS ESI: [M+H]+ m/z 175.0.

Workup

  1. stirringThe reaction mixture was stirred for 1 h at room temperature
  2. concentrationconcentrated
  3. custompurified by column chromatography on silica gel (Biotage 50 G, eluting with 0:100 to 100:0 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-72beff94bc854ac59d99973f7453f07d
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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