Lawesson's reagent → 2-(4-Chloro-3-cyanophenyl)thiazolo[5,4-d]pyrimidine

HRID 1877751Notes

Reaction equation

HRID 1877751 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[C:10](Cl)=[N:11][CH:12]=[N:13][CH:14]=2)=O)=[CH:4][C:3]=1[C:18]#[N:19].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[S:29][C:10]3[N:11]=[CH:12][N:13]=[CH:14][C:9]=3[N:8]=2)=[CH:4][C:3]=1[C:18]#[N:19]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 714261974-Chloro-N-(4-chloropyrimidin-5-yl)-3-cyanobenzamide

Product 1

HCID 672131822-(4-Chloro-3-cyanophenyl)thiazolo[5,4-d]pyrimidineYield 130.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The above-obtained 4-chloro-N-(4-chloro-5-pyrimidinyl)-3-cyanobenzamide (7.98 g, 27.2 mmol) and Lawesson's reagent (8.25 g, 20.4 mmol) were suspended in toluene (150 mL). The suspension was refluxed with heating for 8 hours, and cooled to room temperature to filtrate precipitated crystals. The crystals were washed with chloroform (75×2), and air-dried to obtain 7.25 g (yield: 98%) of the subject compound as pale yellow crystals.

Workup

  1. temperatureThe suspension was refluxed
  2. temperaturewith heating for 8 hours
  3. customprecipitated crystals
  4. washThe crystals were washed with chloroform (75×2)
  5. customair-dried

Sources & evidence

ORD record
ord-eaf2ecc185d7494f8b06b7b543360073
Source dataset
uspto-grants-2012_11
Patent number
US08314085B2

Reaction notes

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