Methanesulfonyl chloride → HCID 22648759, compound

HRID 393163Notes

Reaction equation

HRID 393163 reaction equation
[OH:1][CH:2]([C:6]1[C:7]([CH:12]([CH3:14])[CH3:13])=[N:8][CH:9]=[N:10][CH:11]=1)[CH:3]([CH3:5])[CH3:4].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[CH3:15][S:16]([O:1][CH:2]([C:6]1[C:7]([CH:12]([CH3:14])[CH3:13])=[N:8][CH:9]=[N:10][CH:11]=1)[CH:3]([CH3:5])[CH3:4])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22648769HCID 22648769, compound

Product 1

HCID 22648759HCID 22648759, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.3 g (43 mmol) of 5-(1-hydroxy-2-methylpropyl)-4-isopropylpyrimidine was dissolved in 10 ml of pyridine, and under cooling with ice, 9.8 g (86 mmol) of methylsulfonyl chloride was dropwise added. The reaction mixture was reacted at room temperature for 2 hours, and then, 100 ml of ice water was added, followed by extraction with ethyl acetate. The obtained organic layer was washed with an aqueous citric acid solution and water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure to obtain 10.6 g (yield: 90%) of 5-(1-methylsulfonyloxy-2-methylpropyl)-4-isopropylpyrimidine.

Workup

  1. additionwas dropwise added
  2. customThe reaction mixture was reacted at room temperature for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe obtained organic layer was washed with an aqueous citric acid solution and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-038a5740a1de405b83ba2e2f99cae9c3
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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