Triethylamine → Benzyl 4-(4-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)piperidin-1-carboxylate

HRID 20233Notes

Reaction equation

HRID 20233 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)=[C:2]=[O:3].Br.Br[CH2:22][CH2:23][CH:24]([NH2:26])[CH3:25].C(N(CC)CC)C.CC(C)([O-])C.[K+]>C(#N)C.C1COCC1>[CH3:25][CH:24]1[CH2:23][CH2:22][N:1]([CH:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:6][CH2:5]2)[C:2](=[O:3])[NH:26]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2776273Benzyl 4-isocyanatopiperidine-1-carboxylateHCID 135559884-Bromobutan-2-amine hydrobromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 68420479Benzyl 4-(4-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)piperidin-1-carboxylateYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 4-isocyanatopiperidin-1-carboxylate (0.26 g) in acetonitrile (10 mL) was added to a solution of 4-bromobutan-2-amine hydrobromide (0.17 g) and triethylamine (0.10 g) in acetonitrile (10 mL), followed by stirring at room temperature for one hour. Potassium tert-butoxide (0.29 g) and THF (20 mL) were added thereto, and the mixture was further stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1) to obtain the title compound (0.15 g, 45%) as a light brown solid.

Workup

  1. stirringthe mixture was further stirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-dd0ca6057de441808d4ef09f4c6f81e1
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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