Water → 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-isopropyl-benzenesulfonamide

HRID 1366274Notes

Reaction equation

HRID 1366274 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH:12]([CH3:14])[CH3:13])(=[O:10])=[O:9].[H-].[Na+].[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([Cl:25])=[CH:20][N:19]=1.O>CN1C(=O)N(C)CC1>[Cl:17][C:18]1[N:23]=[C:22]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([NH:11][CH:12]([CH3:14])[CH3:13])(=[O:10])=[O:9])[C:21]([Cl:25])=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2372592,4,5-TrichloropyrimidineHCID 167834652-Amino-N-isopropylbenzenesulfonamide

Product 1

HCID 587485602-(2,5-Dichloro-pyrimidin-4-ylamino)-N-isopropyl-benzenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

To a solution of 2-amino-N-isopropyl-benzenesulfonamide (16.1 g, 75.1 mmol) in DMI (150 mL) is added sodium hydride (6.6 g, 165.3 mmol) portionwise at 0° C. After the mixture is stirred at room temperature for one hour, 2,4,5-trichloropyrimidine (20.7 g, 112.7 mmol) is added at 0° C. After further stirring at room temperature for 5 hrs, water is added and the mixture is extracted with AcOEt three times. Organic layer is washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by silica gel column chromatography (Hexane to Hexane:AcOEt=4:1) to afford the title compound as pale brown solid (10.2 g, 38%).

Workup

  1. stirringAfter further stirring at room temperature for 5 hrs
  2. extractionthe mixture is extracted with AcOEt three times
  3. washOrganic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (Hexane to Hexane:AcOEt=4:1)

Sources & evidence

ORD record
ord-5b8a1ea06fbf42c197481483cc40b36d
Source dataset
uspto-grants-2011_02
Patent number
US07893074B2

Reaction notes

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