Ethylamine → HCID 67184314, compound

HRID 45883Notes

Reaction equation

HRID 45883 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15](S(C)(=O)=O)[N:14]=3)[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)=[N:9]2)=[CH:5][CH:4]=1.[CH2:34]([NH2:36])[CH3:35]>O1CCOCC1.O>[CH2:34]([NH:36][C:15]1[N:14]=[C:13]([C:11]2[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)=[N:9][N:8]([CH2:7][C:6]3[CH:32]=[CH:33][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:12]=2)[CH:18]=[CH:17][N:16]=1)[CH3:35]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 67184047HCID 67184047, compound

Product 1

HCID 67184314HCID 67184314, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

450 mg (0.97 mmol) of 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)pyrimidine were dissolved in a mixture of 10 ml of dioxane and 5 ml of ethylamine 70% in water. The resulting solution was submitted to microwave irradiation in a sealed vial at 140° C. for 45 minutes. The solvent was then removed and the residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate. The organic phase was then dried over sodium sulphate and evaporated to dryness. 391 mg (94%) of the title compound were obtained by trituration with diethylether.

Workup

  1. customirradiation in a sealed vial at 140° C. for 45 minutes
  2. customThe solvent was then removed
  3. customthe residue was partitioned between dichloromethane and aqueous sodium hydrogenocarbonate
  4. dry with materialThe organic phase was then dried over sodium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-62ba743d0b6c4d45bf346836ac5f134c
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

Loading…