Water → 4-Chlorothieno[2,3-d]pyrimidine

HRID 718308Notes

Reaction equation

HRID 718308 reaction equation
CN(C=O)C.[C:6]([Cl:11])(=O)[C:7](Cl)=O.[N:12]1[C:17]2[S:18][CH:19]=[CH:20]C=2C(=O)[NH:14][CH:13]=1.O>ClCCl>[Cl:11][C:6]1[C:7]2[CH:20]=[CH:19][S:18][C:17]=2[N:12]=[CH:13][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2808547thieno(2,3-d)pyrimidin-4(3H)-one

Product 1

HCID 7366184-Chlorothieno[2,3-d]pyrimidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DMF (1.53 ml, 19.7 mmol) in dichloromethane (50 ml) was cooled to 0° C. and oxalyl chloride (2.5 ml, 29.6 mmol) was added slowly forming a white gel. Thieno[2,3-d]pyrimidin-4(3H)-one (1.5 g, 9.86 mmol) was added and the reaction mixture was refluxed for 3 hours. The mixture was cooled down to room temperature and poured into water. The mixture was extracted with dichloromethane, dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by silica gel chromatography (EtOAc/hexane 15:1) to yield the title compound as a white solid (1.61 g, 96%).

Workup

  1. customforming a white gel
  2. temperaturethe reaction mixture was refluxed for 3 hours
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by silica gel chromatography (EtOAc/hexane 15:1)

Sources & evidence

ORD record
ord-dfaf0aafd18544e19236060e26113fbc
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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