Water → HCID 58316898, compound

HRID 1187284Notes

Reaction equation

HRID 1187284 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>O1CCCC1>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([S:21]([C:18]3[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=3)(=[O:23])=[O:22])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 148092816-Chloro-7-iodo-7-deazapurine

Product 1

HCID 58316898HCID 58316898, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (27, 2.45 g, 8.77 mmol) in 68 mL of tetrahydrofuran, sodium hydride (0.4208 g, 10.52 mmol) is added and the reaction is stirred at room temperature for 30 minutes. 4-Methyl-benzenesulfonyl chloride (28, 1.838 g, 9.643 mmol) is added and the reaction stirred at room temperature overnight. Water is added and the reaction is extracted with ethyl acetate, resulting in some precipitate that is removed by filtration. The aqueous layer is separated and extracted with ethyl acetate. The organic layers are combined, washed with water, then brine and dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum. The residue is suspended in ethyl acetate, sonicated for 30 minutes, and the solid collected by filtration to provide the desired compound (29, 3.325 g). MS (ESI) [M+H+]+=433.8.

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. extractionthe reaction is extracted with ethyl acetate
  3. customresulting in some precipitate that
  4. customis removed by filtration
  5. customThe aqueous layer is separated
  6. extractionextracted with ethyl acetate
  7. washwashed with water
  8. dry with materialbrine and dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under vacuum
  11. customsonicated for 30 minutes
  12. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-c9d735dbc3fa4806bb9765b5ad7a3e77
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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