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Tetrahydrofuran → Tert-butyl 4-(2-(ethylsulfonyl) quinazolin-7-yloxy)piperidine-1-carboxylate

HRID 2079669
Notes
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Reaction equation

HRID 2079669 reaction equation
C(S[C:4]1[N:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[CH:9][CH:10]=2)[N:5]=1)C.O[O:29][S:30]([O-:32])=O.[K+].[CH2:34]1COC[CH2:35]1>O>[CH2:34]([S:30]([C:4]1[N:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17][CH2:16]3)=[CH:9][CH:10]=2)[N:5]=1)(=[O:32])=[O:29])[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 67101955Tert-butyl 4-(2-(ethylthio)quinazolin-7-yloxy)piperidine-1-carboxylate

Product 1

HCID 67102269Tert-butyl 4-(2-(ethylsulfonyl) quinazolin-7-yloxy)piperidine-1-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 4-(2-(ethylthio) quinazolin-7-yloxy)piperidine-1-carboxylate (1 eq) in THF (5 ml) was added a solution of oxone in water (5 ml) at 0° C. The reaction mixture was stirred for 30 min at 0° C. then warmed to room temperature and stirred for 4 h. The reaction was quenched with satd. sodium thiosulfate solution and basified with 1N NaOH. The product was extracted from basic layer with DCM. The DCM extracts were combined together, washed with brine and dried over sodium sulfate. The purification by flash column chromatography (70% EtOAc/Hexane) provide pure product in 60% yield. ES/MS m/z 422.0 (MH+).

Workup

  1. temperaturethen warmed to room temperature
  2. stirringstirred for 4 h
  3. customThe reaction was quenched with satd
  4. extractionThe product was extracted from basic layer with DCM
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe purification by flash column chromatography (70% EtOAc/Hexane)
  8. customprovide pure product in 60% yield

Sources & evidence

ORD record
ord-a5c2aa3e3df84734893f40bc46cd8b66
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932262B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes