1,4-Dioxane → HCID 54072696, compound

HRID 354014Notes

Reaction equation

HRID 354014 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[CH2:5][N:6]([CH3:26])[C:7]([C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][N:12]=[C:11](S(C)(=O)=O)[N:10]=1)=[O:8].O1[CH2:36][CH2:35]OCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[CH2:5][N:6]([CH3:26])[C:7]([C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][N:12]=[C:11]([N:10]2[CH2:36][CH2:35][N:6]([CH3:5])[CH2:7][CH2:9]2)[N:10]=1)=[O:8]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 54071226HCID 54071226, compound

Product 1

HCID 54072696HCID 54072696, compoundYield 89%

Procedure

To a solution of 0.25 g (0.538 mmol) 2-methylsulfonyl-5-o-tolyl-pyrimidine-4-carboxylic acid (3,5-dichloro-benzyl)-methyl-amide in 5 ml dioxane 0.15 ml (1.34 mmol) 1-methylpiperazine was added. The reaction mixture was stirred for 16 hrs. After evaporation of the solvent, the residue was distributed between 25 ml CH2Cl2 and 25 ml H2O. The aqueous layer was extracted with 20 ml CH2Cl2, the combined organic layers dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH) 9:1) to give 0.116 g (44%) 2-(4-methyl-piperazin-1-yl)-5-o-tolyl-pyrimidine-4-carboxylic acid (3,5-dichloro-benzyl)-methyl-amide as a colorless oil, MS (ISP): 484.3, 486.3 (M+H+).

Workup

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous layer was extracted with 20 ml CH2Cl2
  3. dry with materialthe combined organic layers dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH) 9:1)

Sources & evidence

ORD record
ord-16e38629322044209485c11141d224c0
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

Loading…