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

HRID 2281362Notes

Reaction equation

HRID 2281362 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.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([I:11])=[CH:9][N:8]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 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 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,4-dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.80 g, 5.73 mmol) in DCM (20 ml) was added TsCl (1.09 g, 5.73 mmol) and TEA (1.60 mL, 11.46 mmol), followed by DMAP (70 mg, 0.573 mmol). After stirring for 1 h at room temperature, the solution was concentrated, and the residue was partitioned between EtOAc and H2O, the organic layer was separated, washed with 1N HCl, 5% NaHCO3, dried 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 EtOAc and H2O
  3. customthe organic layer was separated
  4. washwashed with 1N HCl, 5% NaHCO3
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-66339f49e1ea4d5d8048d55487d8c0d3
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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