Potassium Iodide → HCID 89655329, compound

HRID 1750876Notes

Reaction equation

HRID 1750876 reaction equation
[CH3:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[I-].[K+].[C:33]([O-:36])(=[O:35])[CH3:34].[Na+]>C1C=CC=CC=1.CN(C=O)C>[C:33]([O:36][CH2:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[CH:10][C:5]=2[S:4][CH:3]=1)(=[O:35])[CH3:34]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 517045Sodium Acetate2×HCID 552806237-Methylthieno[3,2-d]pyrimidine

Product 1

HCID 89655329HCID 89655329, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

7-methyl-thieno[3,2-d]pyrimidine (500 mg, 3.33 mmol) was dissolved in benzene (11 mL), added with NBS (539 mg, 3.33 mmol) and AIBN (27 mg, 0.17 mmol), and refluxed for 2 hours at 75° C. The reaction mixture was slowly cooled to room temperature, and added with potassium iodide (553 mg, 3.33 mmol) and DMF (5 mL), followed by stirring for 1 hour at 40° C. Sodium acetate (273 mg, 3.33 mmol) was added thereto, followed by further stirring for 3 hour at 40° C. Additionally, sodium acetate (273 mg, 3.33 mol) was added thereto, and the reaction mixture was stirred for 12 hours at 40° C. The reaction mixture was subjected to extraction with ethyl acetate, washed with water and NaS2O3 solution, dried and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (ethyl acetate:hexane=1:1 (v/v)) to obtain the title compound (140 mg, 20%).

Workup

  1. temperatureThe reaction mixture was slowly cooled to room temperature
  2. stirringby further stirring for 3 hour at 40° C
  3. stirringthe reaction mixture was stirred for 12 hours at 40° C
  4. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  5. washwashed with water and NaS2O3 solution
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrated compound was purified

Sources & evidence

ORD record
ord-1261435b1190446c947379ddb32aae8e
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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