4-Toluenesulfonyl chloride → 4-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1876740Notes

Reaction equation

HRID 1876740 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][C:13]1[C:14]2[CH:21]=[CH:20][NH:19][C:15]=2[N:16]=[CH:17][N:18]=1.[OH-].[Na+]>CC(C)=O>[Cl:12][C:13]1[C:14]2[CH:21]=[CH:20][N:19]([S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidineYield 162.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

To a clean, dry, nitrogen-purged reactor were charged acetone (87.5 ml), p-toluenesulfonyl chloride (17.1 g, 0.09 mol) and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (25.0 g, 0.16 mol). The reactor was cooled to between −5.0 to 5.0° C. and 2.5 M sodium hydroxide (78.1 ml) was added at a rate to maintain the temperature below 5.0° C. The reactor was warmed to between 20-30° C. and stirred for a minimum of 5 hours. The resulting solids were isolated by filtration and washed with acetone/water (1:1, 25 ml each). After drying for a minimum of 12 hours under vacuum at 40-50° C. with slight nitrogen bleed, 44.9 g (90.1%) of the title compound were isolated.

Workup

  1. customTo a clean, dry
  2. customnitrogen-purged reactor
  3. additionwas added at a rate
  4. temperatureto maintain the temperature below 5.0° C
  5. customThe resulting solids were isolated by filtration
  6. washwashed with acetone/water (1:1, 25 ml each)
  7. customAfter drying for a minimum of 12 hours under vacuum at 40-50° C. with slight nitrogen

Sources & evidence

ORD record
ord-79cde6a3d490482dae8102185b806aeb
Source dataset
uspto-grants-2012_11
Patent number
US08309716B2

Reaction notes

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