Sodium hydride → 2,5-dichloro-N-(2-(difluoromethylsulfonyl)phenyl)-pyrimidin-4-amine

HRID 2046960Notes

Reaction equation

HRID 2046960 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[F:10][CH:11]([F:22])[S:12]([C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17])(=[O:14])=[O:13].[H-].[Na+].C(Cl)Cl.CO>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[S:12]([CH:11]([F:22])[F:10])(=[O:14])=[O:13])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2372592,4,5-TrichloropyrimidineHCID 7105932-DifluoromethanesulfonylanilineHCID 21226129Dichloromethane methanol

Product 1

HCID 582908972,5-dichloro-N-(2-(difluoromethylsulfonyl)phenyl)-pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,5-trichloropyrimidine (1 mmol) and 2-(difluoromethylsulfonyl)aniline (1 mmol) in 10 mL of DMF was added sodium hydride (2 mmol) at 0° C. After the reaction mixture was warmed to room temperature and stirred at 50° C. for 1 hour. After work-up and flash chromatography (CH2Cl2/MeOH 9:1), product was obtained. MS (ES+): 353.96 (M+1)+.

Sources & evidence

ORD record
ord-8f7e921ecd4145e88800096676bf96c5
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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