4-Toluenesulfonyl chloride → 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 645702Notes

Reaction equation

HRID 645702 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([I:11])=[CH:9][NH:8][C:6]=2[N:7]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([I:11])=[CH:9][N:8]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 574159022,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 579902932,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidineYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,4-dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.80 g, 5.73 mmol) in CH2Cl2 (20 mL) was added p-toluenesulfonyl chloride (TsCl) (1.09 g, 5.73 mmol) and triethylamine (TEA) (1.60 mL, 11.46 mmol), followed by dimethylaminopyridine (DMAP) (70 mg, 0.573 mmol). After stirring for 1 h at room temperature, the solution was concentrated, and the residue was partitioned between ethyl acetate and H2O. The organic layer was separated, washed sequentially with 1N HCl and 5% NaHCO3. The organic extracts were dried over Na2SO4 and concentrated to give 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (2.0 g).

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and H2O
  3. customThe organic layer was separated
  4. washwashed sequentially with 1N HCl and 5% NaHCO3
  5. dry with materialThe organic extracts were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a9c98a259f1e4c489f40a0faf2001401
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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