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

HRID 1805881Notes

Reaction equation

HRID 1805881 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-39d9ea3fda4b4370b2677593a5bbf7a8
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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