1-Methylpiperazine → HCID 18432500, compound

HRID 2305994Notes

Reaction equation

HRID 2305994 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[C:8](=[O:15])[NH:9][C:10](SC)=[N:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[C:8](=[O:15])[NH:9][C:10]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)=[N:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 12051690HCID 12051690, compound

Product 1

HCID 18432500HCID 18432500, compoundYield 37.2%

Procedure

A solution of of 5-(4-chlorophenoxy)-2-(methylmercapto)pyrimidin-4(3H)-one (158 g, 5.87 mmoles) and 1-methylpiperazine (Aldrich) (6.1 mL, 55 mmoles) was heated at 135° C. for 18 hours. The dark brown mixture was spin evaporated in vacuo. The residue was dissolved in ethyl acetate and applied to a column (d=5 cm) of Silica Gel 80 that was equilibrated with ethyl acetate. The column was eluted with ethyl acetate by flash chromatography to remove unreacted starting material. Elution with 10% methanol-dichloromethane and spin evaporation in vacuo of the combined fractions gave a beige solid that was triturated with ethyl acetate to give 0.70 g (37% yield) of 5-(4-chlorophenoxy)-2-(4-methylpiperazino)pyrimidin-4(3H)-one. Recrystallization from ethyl acetate gave off-white flakes that had an NMR spectrum consistent with the assigned structure.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe column was eluted with ethyl acetate by flash chromatography
  4. customto remove unreacted
  5. washElution with 10% methanol-dichloromethane
  6. customevaporation in vacuo of the combined fractions
  7. customgave a beige solid
  8. customthat was triturated with ethyl acetate

Sources & evidence

ORD record
ord-07cfc3c401f3491bbd398ab5ba052a36
Source dataset
uspto-grants-2002_08
Patent number
US06440965B1

Reaction notes

Loading…