Dichloromethane → HCID 53307901, compound

HRID 445925Notes

Reaction equation

HRID 445925 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[C:10]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:9]=2)=[CH:4][CH:3]=1.[Cl:25]CCl.C(N(CC)CC)C.CS(Cl)(=O)=O>O>[Cl:25][CH2:14][C:13]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][C:10]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[N:11][C:12]=1[CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 9819937N-(4-(4-fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

Product 1

HCID 53307901HCID 53307901, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[4-(4-fluorophenyl)-5-hydroxymethyl-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (50.0 g), dichloromethane (250.0 mL), and triethylamine (47.3 mL) were added to a reactor and then the reaction mixture was cooled to 0˜5° C. Methanesulfonyl chloride (13.2 mL) was slowly added to the reaction mixture, which was then stirred at 20˜25° C. for 5 hours. Water (100.0 mL) was added to the reaction mixture. The separated organic layer was sequentially washed with 0.5N hydrochloric acid solution (100.0 mL) and then water (100.0 mL). The organic layer was concentrated under reduced pressure to remove the solvent. n-Hexane (150.0 mL) was added to the resulting residue under stirring. The resulting suspension was filtered under reduced pressure. The resulting white solid was dried to obtain N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (45.5 g, yield 88%).

Workup

  1. temperaturethe reaction mixture was cooled to 0˜5° C
  2. washThe separated organic layer was sequentially washed with 0.5N hydrochloric acid solution (100.0 mL)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customto remove the solvent
  5. additionn-Hexane (150.0 mL) was added to the resulting residue
  6. stirringunder stirring
  7. filtrationThe resulting suspension was filtered under reduced pressure
  8. customThe resulting white solid was dried

Sources & evidence

ORD record
ord-b16b5384d7dd43aca7ce03d197b32ff1
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Reaction notes

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