Diisopropylethylamine → Tert-butyl 4-{[6-chloro-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

HRID 717881Notes

Reaction equation

HRID 717881 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[Cl:24][C:25]1[CH:30]=[C:29](Cl)[N:28]=[C:27]([C:32]([F:35])([F:34])[F:33])[N:26]=1>C(Cl)Cl.O>[Cl:24][C:25]1[N:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[N:28]=[C:29]([NH:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:30]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 157131974,6-Dichloro-2-trifluoromethylpyrimidine

Product 1

HCID 86706861Tert-butyl 4-{[6-chloro-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-aminopiperidine-1-carboxylate (1.4 g, 7.1 mmol, Aldrich) was dissolved in methylene chloride (10. mL) and to this solution was added N,N-diisopropylethylamine (2.5 mL, 14 mmol) and 4,6-dichloro-2-(trifluoromethyl)pyrimidine (1.7 g, 7.8 mmol, Synchem). The reaction was stirred overnight. The mixture was diluted with water and the product was extracted with EtOAc. The organic layer was washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated to afford product which was used without further purification in Step 2. LCMS (M+H)+: 381.1.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed twice with water, once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford product which
  7. customwas used without further purification in Step 2

Sources & evidence

ORD record
ord-52d7c2cab18c4fe4b12dea61ef15a833
Source dataset
uspto-grants-2015_11
Patent number
US09193733B2

Reaction notes

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