Imidazole → 4-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine

HRID 410708Notes

Reaction equation

HRID 410708 reaction equation
N1C=CN=C1.[Cl:6][C:7]1[N:12]=[C:11]([O:13][CH2:14][CH2:15][OH:16])[CH:10]=[CH:9][N:8]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>ClCCl>[Si:17]([O:16][CH2:15][CH2:14][O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([Cl:6])[N:12]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 597640682-[(2-Chloropyrimidin-4-yl)oxy]ethanol

Product 1

HCID 866582614-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (389 mg, 5.72 mmol) was added to a suspension of 2-[(2-chloropyrimidin-4-yl)oxy]ethanol (416 mg, 2.38 mmol) in dichloromethane (9.5 mL) at 0° C. tert-Butyldimethylsilyl chloride (424 mg, 2.81 mmol) was added and the reaction mixture stirred at room temperature for 2 h. The reaction was quenched with water and the organic layer separated. The organic layer was dried over sodium sulfate, filtered, and concentrated to give 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine (678 mg, 2.35 mmol, 99% yield) as a clear, yellow oil. MS ESI: [M+H]+ m/z 289.1.

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. customthe organic layer separated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1664ba557db24ec4a2aa7f4959c404c6
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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