Water → HCID 68780831, compound

HRID 2264412Notes

Reaction equation

HRID 2264412 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][N:3]=1.[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.C(N(CC)CC)C.O>C(O)CO>[CH2:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][CH:11]([NH:10][C:2]2[N:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][N:3]=2)[CH2:16][CH2:15]1)=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 68780831HCID 68780831, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 2-chloro-5-ethylpyrimidine (5.0 g, 35.1 mmol, 1.0 equiv; commercially available), ethyl 4-amino-1-piperidine carboxylate (7.2 g, 42.1 mmol, 1.2 equiv) and triethylamine (5.3 g, 52.7 mmol, 1.5 equiv) in ethylene glycol (60 mL) was heated by microwave irradiation to 200° C. for 15 min. To the crude reaction mixture was added water (120 mL) and the solution extracted with dichloromethane (3×20 mL). The combined organic layers were washed with water (20 mL) and a sat. solution of sodium chloride (20 mL), dried over MgSO4 and evaporated under reduced pressure to give an amber oil. The residue was purified by column chromatography on silica eluting with heptane/ethyl acetate (1:1) followed by recrystallization from heptane (200 mL) to afford 4.53 g (46%) of the title compound as a white solid. MS (ISP): 279.3 [M+H]+.

Workup

  1. customTo the crude reaction mixture
  2. extractionthe solution extracted with dichloromethane (3×20 mL)
  3. washThe combined organic layers were washed with water (20 mL)
  4. dry with materiala sat. solution of sodium chloride (20 mL), dried over MgSO4
  5. customevaporated under reduced pressure
  6. customto give an amber oil
  7. customThe residue was purified by column chromatography on silica eluting with heptane/ethyl acetate (1:1)
  8. customfollowed by recrystallization from heptane (200 mL)

Sources & evidence

ORD record
ord-083eb8726bb944eba6d18ed364a476d8
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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