p-Bromobenzenesulfonyl chloride → HCID 5081760, compound

HRID 896889Notes

Reaction equation

HRID 896889 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 79782-Aminopyrimidine

Product 1

HCID 5081760HCID 5081760, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromobenzene sulfonyl chloride (3.0 g, 11.74 mmol) and 2-aminopyrimidine (1.17 g, 12.3 mmol, 1.05 eq) in anhydrous pyridine (23 mL) was stirred at 50° C. for 17 hours. The reaction was quenched with 2N aqueous hydrochloric acid (100 mL) and the resultant reaction mixture was extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with water (1×100 mL) and brine (1×100 mL), dried (Na2SO4), filtered, and evaporated under reduced pressure. Recrystallization from ethyl acetate-dichloromethane gave the desired product as a white solid (2.95 g, 80%). LC-MS (ES MH+=314/316); TLC (Rf=0.42, 75% ethyl acetate-hexane).

Workup

  1. customThe reaction was quenched with 2N aqueous hydrochloric acid (100 mL)
  2. customthe resultant reaction mixture
  3. extractionwas extracted with ethyl acetate (2×150 mL)
  4. washThe combined organic layers were washed with water (1×100 mL) and brine (1×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customRecrystallization from ethyl acetate-dichloromethane

Sources & evidence

ORD record
ord-b4d270d6865b4faf8350f636e90784d0
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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