4-Amino-1-Boc-piperidine → HCID 68779241, compound

HRID 2264429Notes

Reaction equation

HRID 2264429 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 51523232-Chloro-4,6-dimethoxypyrimidine

Product 1

HCID 68779241HCID 68779241, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-4,6-dimethoxy-pyrimidine (3.35 g, 19.19 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 24.94 mmol, 1.3 equiv; commercially available) in anhydrous DMF (100 mL) was heated to 100° C. for 48 h. The organic phase was concentrated under reduced pressure and the residue extracted with ethyl acetate (3×50 mL) from a solution of 1 M NaOH (100 mL). The combined organic phases were dried over MgSO4 and the product purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 1.97 g (30%) of the title compound. MS (ISP): 339.3 [M+H]+.

Workup

  1. concentrationThe organic phase was concentrated under reduced pressure
  2. extractionthe residue extracted with ethyl acetate (3×50 mL) from a solution of 1 M NaOH (100 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe product purified by silica column chromatography
  5. washeluting with a gradient of heptane/ethyl acetate providing 1.97 g (30%) of the title compound

Sources & evidence

ORD record
ord-10cd4f85ff914db9baa0d113ac221015
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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