2-Chloropyrimidine → tert-butyl 4-(pyrimidin-2-ylamino)piperidine-1-carboxylate

HRID 1357903Notes

Reaction equation

HRID 1357903 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.Cl[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1.CCN(C(C)C)C(C)C>C(O)(C)C.C(Cl)Cl>[N:17]1[CH:18]=[CH:19][CH:20]=[N:21][C:16]=1[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 2763949tert-butyl 4-(pyrimidin-2-ylamino)piperidine-1-carboxylateYield 36.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-Amino-1-t-butoxycarbonylpiperidine from Step A, (1.9 g, 9.5 mmol), 2-chloropyrimidine (1.1 g, 9.5 mmol) and DIPEA (3.3 mL, 19 mmol) were combined in isopropanol (10 mL) and the mixture was refluxed for 24 h. The mixture was cooled, diluted with methylene chloride (100 mL) and washed with water and brine. The organic phase was dried over sodium sulfate and concentrated. FC (60 g silica, 1/1 hexanes/ethyl acetate) afforded the title compound (0.97 g).

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. temperatureThe mixture was cooled
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5428918efbe041efa28d99971b373f6e
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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