1,4-Dioxane → HCID 178422843, compound

HRID 1514425Notes

Reaction equation

HRID 1514425 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH3:17])[CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[O:18]1CCOCC1>>[CH3:17][C:13]1[CH:12]=[C:11]([C:9]2[CH:8]=[CH:7][NH:6][C:5](=[O:18])[N:10]=2)[CH:16]=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 59242799HCID 59242799, compound

Product 1

HCID 178422843HCID 178422843, compoundYield 52%

Procedure

2-Methanesulfonyl-4-(2-methyl-pyridin-4-yl)-pyrimidine (720 mg, 2.89 mmol) was dissolved in dioxane (25 ml) and then 2N NaOHaq (14.4 ml, 28.9 mmol) was added. After stirring at room temperature for 2 hours, the solution was acidified with 37% HClaq. The mixture was evaporated and the residue was re-dissolved in DCM-MeOH—NH4OH (90-10-1) and evaporated. The crude was purified by flash chromatography with DCM-MeOH (9-1) to give 279 mg of the title compound. (52% yield).

Workup

  1. addition2N NaOHaq (14.4 ml, 28.9 mmol) was added
  2. customThe mixture was evaporated
  3. dissolutionthe residue was re-dissolved in DCM-MeOH—NH4OH (90-10-1)
  4. customevaporated
  5. customThe crude was purified by flash chromatography with DCM-MeOH (9-1)

Sources & evidence

ORD record
ord-a4c1af6aa4a74c779f525b1a9ec0fb66
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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