Dimethyl Sulfoxide → N-[2-(Acetylamino)pyrimidin-5-yl]-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

HRID 2263089Notes

Reaction equation

HRID 2263089 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)=[CH:7][N:6]=1)(=[O:3])[CH3:2].[C:20]1([C:26]2[N:27]=[C:28]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[S:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:1]([NH:4][C:5]1[N:6]=[CH:7][C:8]([NH:11][C:12]([N:34]2[CH2:35][CH2:36][N:31]([C:28]3[S:29][CH:30]=[C:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:27]=3)[CH2:32][CH2:33]2)=[O:19])=[CH:9][N:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 866254942,2,2-Trichloroethyl [2-(acetylamino)pyrimidin-5-yl]carbamate

Product 1

HCID 68779904N-[2-(Acetylamino)pyrimidin-5-yl]-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl [2-(acetylamino)pyrimidin-5-yl]carbamate (60.0 mg, 0.187 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (44.9 mg, 0.183 mmol), diisopropylethylamine (0.0319 ml, 0.183 mmol) and dimethylsulfoxide (2 ml) was stirred at 80° C. for 4 hours, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of tetrahydrofuran, ethyl acetate and hexane to obtain the desired product (31.0 mg, 40.0%) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of tetrahydrofuran, ethyl acetate and hexane

Sources & evidence

ORD record
ord-e3642025ccc84889905002bd0f4bc1a6
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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