Potassium Carbonate → HCID 55251702, compound

HRID 2403574Notes

Reaction equation

HRID 2403574 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 55251702HCID 55251702, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-chloropyrimidine (400 mg) was dissolved in DMF (4 ml), and thiomorpholine 1,1-dioxide (308 mg) and K2CO3 (857 mg) were added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 4-(5-bromopyrimidin-2-yl)thiomorpholine 1,1-dioxide (191 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added
  3. extractionfollowed by extraction with CHCl3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-53d1aea0ab804f4c92e60635a5fb34b5
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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