Chlorosuccinimide → HCID 86719382, compound

HRID 510338Notes

Reaction equation

HRID 510338 reaction equation
[I:1][C:2]1[C:10]2[C:9]([NH2:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[CH:3]=1.C1C(=O)N([Cl:28])C(=O)C1>CN(C=O)C>[Cl:28][C:3]1[N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH2:11])[C:10]=2[C:2]=1[I:1]

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 71217685HCID 71217685, compound

Product 1

HCID 86719382HCID 86719382, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-iodo-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (17) (1.6 g, 4.2 mmol) in DMF (30 mL) was added NCS (840 mg, 6.3 mmol). The resulting mixture was stirred at r.t. overnight. Another portion of NCS (560 mg, 4.2 mmol) was introduced. After the stifling was continued for 8 hrs, the reaction was quenched with water (100 mL). The resulting white precipitates was collected by filtration to afford 6-chloro-5-iodo-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (18) (1.7 g, 91% yield) as a yellow solid. LC-MS (ESI): m/z (M/M+2) 414.6/416.6.

Workup

  1. waitAfter the stifling was continued for 8 hrs
  2. customthe reaction was quenched with water (100 mL)
  3. customThe resulting white precipitates
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-cc4aee052979418aa0fc57eedeae6eb3
Source dataset
uspto-grants-2015_08
Patent number
US09096604B2

Reaction notes

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