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Imidazole → 4-(4-(2-((Tert-butyl(dimethyl)silyl)oxy)ethyl)piperazin-1-yl)-6-chloro-2-methylpyrimidine

HRID 1526309
Notes
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Reaction equation

HRID 1526309 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]2)[CH:3]=1.N1C=CN=C1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].O>CN(C)C=O>[Si:27]([O:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([CH3:8])[N:5]=2)[CH2:10][CH2:11]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 144795582-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol

Product 1

HCID 1317331604-(4-(2-((Tert-butyl(dimethyl)silyl)oxy)ethyl)piperazin-1-yl)-6-chloro-2-methylpyrimidineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol obtained in Step A (1.00 g) and imidazole (0.636 g) in N,N-dimethylformamide (13 mL) was added tert-butyl(chloro)dimethylsilane (0.793 g) at room temperature, and the mixture was stirred for 2 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.42 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-97b3871dd654444b987b077521d72fca
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085578B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes