Imidazole → 5-[(tert-Butyldimethylsilyl)oxy]-2-chloropyrimidine

HRID 632604Notes

Reaction equation

HRID 632604 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>CN(C)C=O>[Si:14]([O:8][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[N:7][CH:6]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 145957002-Chloro-5-pyrimidinol

Product 1

HCID 1317354365-[(tert-Butyldimethylsilyl)oxy]-2-chloropyrimidineYield 104.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 20.2 g (0.154 mol) of 2-chloro-5-hydroxypyrimidine in 150 ml of N,N-dimethylformamide, 15.8 g (0.232 mol) of imidazole and 26.8 g (0.178 mol) of tert-butyldimethylsilyl chloride were added, and the reaction mixture was stirred at room temperature for 2.5 hours. After completion of the reaction, the reaction solution was poured into water and extracted with n-heptane three times. The obtained organic phases were combined, washed with 0.01 N sodium hydroxide aqueous solution, water and saturated sodium chloride aqueous solution in order and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to provide 39.5 g of the title compound as a white solid (yield: 100%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with n-heptane three times
  3. washwashed with 0.01 N sodium hydroxide aqueous solution, water and saturated sodium chloride aqueous solution in order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9e8024b7c7dc46388c46a10cbd530cd2
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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