Methyl iodide → 7-Benzyl-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4(4aH)-one

HRID 971223Notes

Reaction equation

HRID 971223 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=O)[C:11](=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:21][C:22]([NH2:24])=[S:23].[CH3:25][O-].[Na+].IC>CO>[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]2[C:11](=[N:21][C:22]([S:23][CH3:25])=[N:24][C:15]2=[O:17])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2723790ThioureaHCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 692223017-Benzyl-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4(4aH)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride (8.9 g, 30 mmol) and thiourea (4.56 g, 60 mmol) in a solution of sodium methoxide in methanol (34 mL, 25% wt/wt) was stirred at 100° C. in a sealed tube overnight. Iodomethane (5.1 g, 42 mmol) was added dropwise to the reaction mixture after cooling to room temperature and stirred at room temperature for 1 hr. Solvent was removed in vacuo and the residue was dissolved in water (100 mL), extracted by CHCl3 and i-PrOH (3:1, 10×40 mL) and dried over sodium sulfate. Solvent was removed in vacuo, product was obtained as a beige powder (7.6 g).

Workup

  1. temperatureafter cooling to room temperature
  2. stirringstirred at room temperature for 1 hr
  3. customSolvent was removed in vacuo
  4. dissolutionthe residue was dissolved in water (100 mL)
  5. extractionextracted by CHCl3 and i-PrOH (3:1, 10×40 mL)
  6. dry with materialdried over sodium sulfate
  7. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-c50c61561fb24fd4b7847fa8b95f1f47
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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