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

HRID 2375812Notes

Reaction equation

HRID 2375812 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.CC(C)([O-])C.[K+].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:25])=[O:24])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 23665647Potassium tert-butoxide

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, 0.065 mol) in THF (300 mL) was added potassium tert-butoxide (9.15 g, 0.082 mol) at r.t. over 5 min. A slight exotherm was noticed and suspension was cooled with the aid of a water bath. Benzenesulfonyl chloride (10.5 mL, 0.082 mol) was then added drop-wise over a period of 10 min and the resulting suspension stirred for a further 3 h. Then water (20 mL) was added drop-wise and the solution was then stirred for 15 min. The solvent was evaporated under reduced pressure and the reaction mixture was eluted with ethyl acetate (1.2 l), washed with brine (2×100 mL), dried and concentrated. The resulting solid was triturated with ethyl acetate (50 mL) to afford 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 6.75 (1H, d), 7.55-7.625 (2H, t), 7.70 (1H, t), 7.82 (1H, d), 8.25 (1H, d) and 8.80 (1H, s).

Workup

  1. temperaturesuspension was cooled with the aid of a water bath
  2. stirringthe solution was then stirred for 15 min
  3. customThe solvent was evaporated under reduced pressure
  4. washthe reaction mixture was eluted with ethyl acetate (1.2 l)
  5. washwashed with brine (2×100 mL)
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting solid was triturated with ethyl acetate (50 mL)

Sources & evidence

ORD record
ord-d25417f16c444a55bac5409297c709a5
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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