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Tert-butyl 4-(5-benzyl-4-(trifluoromethylsulfonyloxy)pyrimidin-2-yl)piperazine-1-carboxylate → Tert-butyl 4-(5-benzyl-4-methylpyrimidin-2-yl)piperazine-1-carboxylate

HRID 522683
Notes
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Reaction equation

HRID 522683 reaction equation
[CH2:1]([C:8]1[C:9](OS(C(F)(F)F)(=O)=O)=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][Mg]Cl>C1COCC1.CN1CCCC1=O.C(OCC)(=O)C.[NH4+].[Cl-].C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe]>[CH2:1]([C:8]1[C:9]([CH3:35])=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 2

HCID 118023160Tert-butyl 4-(5-benzyl-4-(trifluoromethylsulfonyloxy)pyrimidin-2-yl)piperazine-1-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 118022982Tert-butyl 4-(5-benzyl-4-methylpyrimidin-2-yl)piperazine-1-carboxylateYield 121.2%

Reagents, catalysts & solvents 5

HCID 11110968Iron (III) acetylacetonateCatalyst
HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent
HCID 25517Ammonium ChlorideSolvent

Procedure

To a mixture of tert-butyl 4-(5-benzyl-4-(trifluoromethylsulfonyloxy)pyrimidin-2-yl)piperazine-1-carboxylate (280 mg, 0.56 mmol) and iron (III) acetylacetonate (21 mg, 0.06 mmol) in THF (5 mL, dry) and 1-methyl-2-pyrrolidinone (1 mL) was added methylmagnesium chloride (1.68 mL, 1.68 mmol). The reaction mixture was stirred at RT for 1 h, and diluted with ethyl acetate (100 mL) and sat. aq. NH4Cl (100 mL). The organic layer was washed with brine (100 mL), dried over sodium sulfate, filtered and evaporated to give tert-butyl 4-(5-benzyl-4-methylpyrimidin-2-yl)piperazine-1-carboxylate (crude, 250 mg) as a yellow solid. MS (ES+) C21H28N4O2 requires: 368, found: 369 [M+H]+.

Workup

  1. washThe organic layer was washed with brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-07ee6dd26224470fa601ecac5dcca975
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09334263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes