Chlorosuccinimide → HCID 86719382, compound

HRID 2175647Notes

Reaction equation

HRID 2175647 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-6f6a8106bc2c430cbdba0d671f9991c8
Source dataset
uspto-grants-2015_06
Patent number
US09062058B2

Reaction notes

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