4,6-Dichloro-2-ethylpyrimidine → 1-(2-Ethylpyrimidin-4-yl)-4-methyl-piperidine-4-carboxylic acid

HRID 2289550Notes

Reaction equation

HRID 2289550 reaction equation
[CH3:1][C:2]1([C:8]([O:10]CC)=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:13]([C:15]1[N:20]=[C:19](Cl)[CH:18]=[C:17](Cl)[N:16]=1)[CH3:14]>C(O)C.CCN(CC)CC>[CH2:13]([C:15]1[N:20]=[C:19]([N:5]2[CH2:4][CH2:3][C:2]([CH3:1])([C:8]([OH:10])=[O:9])[CH2:7][CH2:6]2)[CH:18]=[CH:17][N:16]=1)[CH3:14]

Participants

5

Reactant 2

HCID 5184654,6-Dichloro-2-ethylpyrimidineHCID 19361805Ethyl 4-methylpiperidine-4-carboxylate

Product 1

HCID 186980471-(2-Ethylpyrimidin-4-yl)-4-methyl-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8471TriethylamineSolvent

Procedure

1-(2-Ethylpyrimidin-4yl)-4-methyl-piperidine-4-carboxylic acid was prepared on a 3 mmol 4-methyl-4-ethoxycarbonyl-piperidine (as TFA salt) in 7 ml ethanol and 1 ml Et3N treated with a solution of 0.531 g 2-ethyl-4,6-dichloropyrimidine in 4 ml ethanol. After 20 hours at ambient temp. The ethanol was removed and the residue partitioned between water and ethanol, washed with sodium hydrogen carbonate solution and brine. Evaporated to give gum (88.3%).

Workup

  1. customThe ethanol was removed
  2. customthe residue partitioned between water and ethanol
  3. washwashed with sodium hydrogen carbonate solution and brine
  4. customEvaporated

Sources & evidence

ORD record
ord-612357af215049ceae5b4f7b5693025e
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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