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

HRID 595154Notes

Reaction equation

HRID 595154 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][N:3]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>ClCCl.O>[Si:17]([O:11][CH2:10][CH2:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

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-chloropyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-[(2-Chloropyrimidin-4-yl)oxy]ethanol (416 mg, 2.38 mmol) in dichloromethane (9.5 mL) at 0° C. was added to an oven-dried, nitrogen cooled vial containing imidazole (389 mg, 5.72 mmol). The solution was stirred for 10 minutes. TBS-Cl (424 mg, 2.81 mmol) was added and the reaction mixture was stirred at room temperature for 2 h then, diluted with water. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine as a clear, yellow oil. MS ESI calcd. for C12H22ClN2O2Si [M+H]+ 289. found 289. 1H NMR (500 MHz, CDCl3) δ 8.28 (d, J=5.7, 1H), 6.67 (d, J=5.7, 1H), 4.62-4.30 (m, 2H), 4.02-3.87 (m, 2H), 0.87 (s, 9H), 0.06 (s, 6H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8887a829e2747b3b71bd83480a28089
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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