Phosphorus oxychloride → 4-Chloro-7-methylthieno(3,2-d)pyrimidine

HRID 1750874Notes

Reaction equation

HRID 1750874 reaction equation
[CH3:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[S:4][CH:3]=1.O=P(Cl)(Cl)[Cl:14]>CN(C=O)C>[Cl:14][C:10]1[C:5]2[S:4][CH:3]=[C:2]([CH3:1])[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354396367-methyl-3H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 27775864-Chloro-7-methylthieno(3,2-d)pyrimidineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

7-methyl-3H-thieno[3,2-d]pyrimidin-4-one (9 g, 54.2 mmol), DMF (1 mL), POCl3 (80 mL) were mixed and refluxed for 4 hours at 110° C. The reaction solution was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure. The reaction mixture was added with toluene, and further concentrated under reduced pressure. The resulting residue was neutralized with sodium bicarbonate, subjected to extraction with ethyl acetate, dried, and filtered to obtain the title compound (8.1 g, 81%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe reaction mixture was added with toluene
  4. concentrationfurther concentrated under reduced pressure
  5. extractionsubjected to extraction with ethyl acetate
  6. customdried
  7. filtrationfiltered

Sources & evidence

ORD record
ord-2182ca9d69954bc89d509df9c63e71c5
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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