Chlorosuccinimide → 4-(4-(4-Acetyl-2,6-dimethylphenoxy)-7-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

HRID 1516861Notes

Reaction equation

HRID 1516861 reaction equation
[C:1]([C:4]1[CH:28]=[C:27]([CH3:29])[C:7]([O:8][C:9]2[C:10]3[NH:26][CH:25]=[CH:24][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[N:14]=2)=[C:6]([CH3:30])[CH:5]=1)(=[O:3])[CH3:2].C1C(=O)N([Cl:38])C(=O)C1>C(Cl)Cl>[C:1]([C:4]1[CH:5]=[C:6]([CH3:30])[C:7]([O:8][C:9]2[C:10]3[NH:26][CH:25]=[C:24]([Cl:38])[C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=3)[N:14]=2)=[C:27]([CH3:29])[CH:28]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 119624034-(4-(4-Acetyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

Product 1

HCID 119624054-(4-(4-Acetyl-2,6-dimethylphenoxy)-7-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrileYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(4-acetyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (13 mg, 0.03 mmol) in CH2Cl2 (1 mL) was added NCS (4.4 mg, 0.03 mmol) and the mixture refluxed for 16 h. After the completion of the reaction, the solvent was concentrated and purified by preparative TLC eluting with hexanes:ethyl acetate (2:1) to give the product (4.2 mg, 30%).

Workup

  1. temperaturethe mixture refluxed for 16 h
  2. customAfter the completion of the reaction
  3. concentrationthe solvent was concentrated
  4. custompurified by preparative TLC
  5. washeluting with hexanes:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-424e4174958540cd8322db2b4e699027
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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