Water → HCID 71630631, compound

HRID 573993Notes

Reaction equation

HRID 573993 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1.O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 775312,4-DichloropyrimidineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylate

Product 1

HCID 71630631HCID 71630631, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2,4-dichloropyrimidine (2.0 g, 13.4 mmol), (R)-tert-butyl 3-aminopiperidine-1-carboxylate (2.7 g, 13.5 mmol) and NN-diisopropylethylamine (2.3 mL, 13.4 mmol) in N,N′-dimethylformamide (15 mL) was stirred and heated overnight at 90° C. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (2.87 g, 68%) as a yellow oil.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-b5afeca2a15141d0ad953241c162e4c6
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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