Water → HCID 58560902, compound

HRID 1408488Notes

Reaction equation

HRID 1408488 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)=O.O>CS(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[N:8]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 58560902HCID 58560902, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Chloropyrimidin-4-amine (50 mg, 0.39 mmol) and 2-bromo-1-(3-nitrophenyl)ethanone (94 mg, 0.39 mmol) were dissolved in 2 mL of DMSO and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into 5 mL of water and it was then extracted with ethyl acetate. The filtrate was dried (Na2SO4) and evaporated. The compound was purified by silica gel column chromatography by using hexane/ethyl acetate (3:1) as eluent (60 mg, 56% Yield). MS m/z 275.00 (M+1).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe filtrate was dried (Na2SO4)
  3. customevaporated
  4. customThe compound was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c90dcabcf80468085717dc31df1ef86
Source dataset
uspto-grants-2014_12
Patent number
US08921336B2

Reaction notes

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