Benzenesulfonyl chloride → 4-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

HRID 1853597Notes

Reaction equation

HRID 1853597 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 109463064-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (10 g, 65.12 mmol, 1.0 eq) in THF (300 mL), NaH (5.30 g, 130.24 mmol, 2 eq) was added at 0° C. After 3 h, benzenesulfonyl chloride (22.53 g, 130.24 mmol, 2 eq) was added. The temperature was warmed to RT and continued for 1 h. The reaction mixture was poured into sat. NH4Cl and extracted with EtOAc. The organic layers were dried, concentrated and purified by column chromatography (eluting with 10% EtOAc in PE) to afford 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine as brown solid (4.5 g, 24% in yield)

Workup

  1. waitcontinued for 1 h
  2. extractionextracted with EtOAc
  3. customThe organic layers were dried
  4. concentrationconcentrated
  5. custompurified by column chromatography (eluting with 10% EtOAc in PE)
  6. customto afford

Sources & evidence

ORD record
ord-7ed68ae3c1344571aa3886f8675df2f9
Source dataset
uspto-grants-2015_02
Patent number
US08962635B2

Reaction notes

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