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

HRID 1516864Notes

Reaction equation

HRID 1516864 reaction equation
[C:1]1([CH3:29])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:9][C:10]1[C:11]2[N:27]([CH3:28])[CH:26]=[CH:25][C:12]=2[N:13]=[C:14]([NH:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[N:15]=1.C1C(=O)N([Cl:37])C(=O)C1>C(Cl)Cl>[Cl:37][C:25]1[C:12]2[N:13]=[C:14]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:15]=[C:10]([O:9][C:2]3[C:1]([CH3:29])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=3[CH3:8])[C:11]=2[N:27]([CH3:28])[CH:26]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 576936284-(4-(Mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

Product 1

HCID 576936384-(7-chloro-4-(mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrileYield 16.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (17.3 mg, 0.05 mmol) in CH2Cl2 (5 mL) was added NCS (6.03 mg, 0.05 mmol) and the resultant mixture was refluxed for 16 h. After completion of the reaction, the solvent was concentrated and purified by preparative TLC, eluting with hexanes:ethyl acetate (3:1), to give the product as an off-white solid (3.4 mg, 6%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe solvent was concentrated
  3. custompurified by preparative TLC
  4. washeluting with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-1f5b723c33f843529e6833fe123a3615
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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