Ethyl 4-amino-1-piperidinecarboxylate → Ethyl 4-[(4-methoxy-2-pyrimidinyl)amino]-1-piperidinecarboxylate

HRID 2264424Notes

Reaction equation

HRID 2264424 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH2:10]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]1)=[O:14])[CH3:11]>CN1C(=O)CCC1>[CH2:10]([O:12][C:13]([N:15]1[CH2:16][CH2:17][CH:18]([NH:21][C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=2)[CH2:19][CH2:20]1)=[O:14])[CH3:11]

Participants

4

Reactant 2

HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 5889352-Chloro-4-methoxypyrimidine

Product 1

HCID 24237580Ethyl 4-[(4-methoxy-2-pyrimidinyl)amino]-1-piperidinecarboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-chloro-4-methoxy-pyrimidine (3.64 g, 25.21 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid ethyl ester (4.34 g, 25.21 mmol, 1.0 equiv; commercially available) in anhydrous NMP (32 mL) was heated by microwave irradiation to 200° C. for 15 min. 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 with column chromatography on silica eluting with heptane/ethyl acetate (1:1) providing 2.93 g (42%) of the title compound. MS (ISP): 281.3 [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 with column chromatography on silica eluting with heptane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-91c896b2649644249f4a01041a0ed3f9
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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