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

HRID 1465001Notes

Reaction equation

HRID 1465001 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]>>[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

3

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)pyrimidine

Conditions

Temperature
110 °C

Procedure

7-Methylthieno[3,2-d]pyrimidine-4(3H)-one (1.5 g) was added to POCl3 (10 mL), and the mixture was stirred at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated and diluted with DCM, and sat. NaHCO3 solution was added thereto. The aqueous layer was extracted with DCM to combine organic layers. The organic layer was dried with MgSO4 and filtered to obtain the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with DCM, and sat. NaHCO3 solution
  4. additionwas added
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialThe organic layer was dried with MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b21986db6f7b434c819bdee033d9e579
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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