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

HRID 2175379Notes

Reaction equation

HRID 2175379 reaction equation
CN(C)C=O.[Cl:6][CH:7](Cl)[CH3:8].C(Cl)(=O)C(Cl)=O.[N:16]1[C:21]2[CH:22]=[CH:23][S:24]C=2C(=O)[NH:18][CH:17]=1>O>[Cl:6][C:7]1[C:8]2[S:24][CH:23]=[CH:22][C:21]=2[N:16]=[CH:17][N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63651,1-DichloroethaneHCID 65578Oxalyl chlorideHCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 27358214-Chlorothieno[3,2-d]pyrimidineYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After dimethylformamide (15.4 ml, 197.13 mmol) was added into 150 ml of dichloroethane with lowering the temperature to 0° C., oxalyl chloride (25 4 ml, 295.70 mmol) was slowly added. When white gel type started to form, 3H-thieno[3,2-d]pyrimidine-4-one (15 g, 98.57 mmol) was added. After 2.5 hours of reflex of the reaction mixture, the temperature was lowed to room temperature. After adding water, the reaction mixture was extracted using dichloromethane (3×300 ml) and dried with anhydrous magnesium sulfate. After concentrated under vacuum, trituration was carried out with 200 ml of hexane and the title compound (16.7 g, 99%) was obtained as a dark brown solid.

Workup

  1. customto 0° C.
  2. customto form
  3. customwas lowed to room temperature
  4. extractionthe reaction mixture was extracted
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationAfter concentrated under vacuum, trituration

Sources & evidence

ORD record
ord-c34409423a144797a05f6f1fa3695d77
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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