1,4-Dioxane → HCID 178432682, compound

HRID 1514421Notes

Reaction equation

HRID 1514421 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[O:18]1CCOCC1>>[CH3:17][C:12]1[C:11]([C:9]2[CH:8]=[CH:7][NH:6][C:5](=[O:18])[N:10]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 59242804HCID 59242804, compound

Product 1

HCID 178432682HCID 178432682, compound

Procedure

2-Methanesulfonyl-4-(2-methyl-pyridin-3-yl)-pyrimidine (446 mg, 1.79 mmol) was dissolved in dioxane (13 ml) and then 2N NaOHaq (8.9 ml, 17.9 mmol) was added. After stirring at room temperature for 1 hour, the solution was acidified with 37% HClaq. The mixture was evaporated and the residue was re-dissolved in DCM-MeOH—NH4OH (95-5-0.5) and evaporated. The crude was purified by flash chromatography with DCM-MeOH (9-1) to give 343 mg of the title compound. (quantitative yield).

Workup

  1. addition2N NaOHaq (8.9 ml, 17.9 mmol) was added
  2. customThe mixture was evaporated
  3. dissolutionthe residue was re-dissolved in DCM-MeOH—NH4OH (95-5-0.5)
  4. customevaporated
  5. customThe crude was purified by flash chromatography with DCM-MeOH (9-1)

Sources & evidence

ORD record
ord-cd0f063023ed4eaa88ffdc13f84f86f9
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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