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Cesium carbonate → Tert-butyl 1'-[2-(trifluoromethyl)pyrimidin-4-yl]-4,4'-bipiperidine-1-carboxylate

HRID 1947656
Notes
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Reaction equation

HRID 1947656 reaction equation
[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[N:28]=1>CN1C(=O)CCC1.C(OCC)(=O)C>[F:34][C:33]([F:36])([F:35])[C:29]1[N:30]=[C:31]([N:10]2[CH2:11][CH2:12][CH:7]([CH:4]3[CH2:5][CH2:6][N:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][CH2:3]3)[CH2:8][CH2:9]2)[CH:32]=[CH:27][N:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 117475994,4'-Bipiperidine, 1-boc protectedHCID 533023444-Bromo-2-(trifluoromethyl)pyrimidine

Product 1

HCID 59178917Tert-butyl 1'-[2-(trifluoromethyl)pyrimidin-4-yl]-4,4'-bipiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
70 °C

Procedure

The tert-butyl 4,4′-bipiperidine-1-carboxylate (28.5 mg, 0.11 mmol) and cesium carbonate (106 mg, 0.32 mmol) were stirred in NMP (0.5 ml) and the 4-bromo-2-(trifluoromethyl)pyrimidine (12 mg, 0.053 mmol) was added. The mixture was heated at 70° C. for 2 h. The reaction was cooled down to r.t. and diluted with ethyl acetate (5 mL) and was washed with water 2 mL (×1) and brine 2 mL (×1). The organic phase was dried over magnesium sulfate, filtered, and concentrated on rotavapor. The crude material was purified by preparative TLC with 30% acetone: hexane to yield the titled compound.

Workup

  1. temperatureThe reaction was cooled down to r.t.
  2. washwas washed with water 2 mL (×1) and brine 2 mL (×1)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on rotavapor
  6. customThe crude material was purified by preparative TLC with 30% acetone

Sources & evidence

ORD record
ord-f44710e0fdbe4ca2997ba5e289987449
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399485B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes