Triethylamine → HCID 50995180, compound

HRID 1399620Notes

Reaction equation

HRID 1399620 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.[NH:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:26][CH2:25]1.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O.[Na+]>[C:31]([NH:30][CH:27]1[CH2:28][CH2:29][N:24]([C:2]2[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]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:3]=2)[CH2:25][CH2:26]1)(=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118120N-4-PiperidylbenzamideHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 50995180HCID 50995180, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

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), N-(piperidin-4-yl)benzamide (0.191 g; 0.937 mmol) and triethyl amine (0.220 mL; 1.56 mmol) in tetrahydrofuran (2 mL) was heated at 110° C. in a sealed tube for 5 h. The reaction mixture was diluted with a saturated solution of sodium hydrogen carbonate, extracted twice with ethyl acetate. The combined 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 (15-80%) in heptane furnished 0.049 g (34%) of the title compound as a colorless oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined 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 (15-80%) in heptane

Sources & evidence

ORD record
ord-fa7043286a3a4c07b61443df83afc3a3
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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