Methyl iodide → Benzyl 4-[3-(2-methoxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

HRID 20237Notes

Reaction equation

HRID 20237 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)[C:7]1=[O:28].[CH3:29]I>C1COCC1.N>[CH3:29][O:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[CH2:14][CH2:13]2)[C:7]1=[O:28]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68420920benzyl 4-[3-(2-hydroxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

Product 1

HCID 68420480Benzyl 4-[3-(2-methoxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil; 71 mg) was added under ice-cooling to a solution of benzyl 4-[3-(2-hydroxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate (0.59 g) obtained in Example 39a) in THF (30 mL), and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (0.11 mL) was added to the reaction mixture, followed by stirring at room temperature for 15 hours. The reaction solution was diluted with an aqueous saturated ammonia solution to separate the organic layer. The organic layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound (0.60 g, quantitative) as a white powder.

Workup

  1. stirringby stirring at room temperature for 15 hours
  2. customto separate the organic layer
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8b172c079f04b0eba0985053dc9f32f
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

Loading…