Triethylamine → HCID 50995369, compound

HRID 1399617Notes

Reaction equation

HRID 1399617 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.[C:24]1([CH:30]2[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O>[CH3:8][C:6]1[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=[C:2]([N:32]2[CH2:33][CH2:34][CH2:35][CH:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:31]2)[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1072073-PhenylpiperidineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 50995369HCID 50995369, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.104 g; 0.312 mmol), 3-phenylpiperidine (0.151 g; 0.937 mmol) and triethylamine (0.220 mL; 1.56 mmol) in tetrahydrofuran (2 mL) was heated to 110° C. in a sealed tube for 5 h. The reaction mixture was diluted with a saturated solution of hydrogen carbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-15%) in heptane furnished 0.047 g (33%) of the title compound as a colorless oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-15%) in heptane

Sources & evidence

ORD record
ord-b05dbf84171b4df4a12fca61fd9910a2
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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