HCID 59812873, compound → HCID 59812953, compound

HRID 230196Notes

Reaction equation

HRID 230196 reaction equation
[CH:1]1([CH:6]([C:8]2[C:9]([Cl:17])=[N:10][C:11]([S:15][CH3:16])=[N:12][C:13]=2[Cl:14])[OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1>CC(C)=O>[CH:1]1([C:6]([C:8]2[C:9]([Cl:17])=[N:10][C:11]([S:15][CH3:16])=[N:12][C:13]=2[Cl:14])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 59812873HCID 59812873, compound

Product 1

HCID 59812953HCID 59812953, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopentyl-(4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)-methanol (8.1 g, 27.62 mmol) was dissolved in 100 mL dry acetone and stirred under nitrogen at 0° C. CrO3 (11.05 g, 110.497 mmol) was added in portions over three minutes. The reaction mixture was stirred for 20 minutes. The reaction was quenched by addition of 15 mL isopropanol, followed by basificaction with saturated aqueous sodium bicarbonate. The resulting solution was filtered through Celite, and the Celite was washed with acetone. The resulting solution was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 3.1 g of Cyclopentyl-(4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)-methanone. Mass Spec. M+H=292.

Workup

  1. stirringThe reaction mixture was stirred for 20 minutes
  2. customThe reaction was quenched by addition of 15 mL isopropanol
  3. filtrationThe resulting solution was filtered through Celite
  4. washthe Celite was washed with acetone
  5. dry with materialThe resulting solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-735ee7d1e00e4f71b60539a6759e5687
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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