Water → 7-Bromo-4-chlorothieno[3,2-d]pyrimidine

HRID 1750862Notes

Reaction equation

HRID 1750862 reaction equation
CN(C)C=O.[C:6]([Cl:11])(=O)[C:7](Cl)=O.[Br:12][C:13]1[C:17]2[N:18]=[CH:19][NH:20]C(=O)C=2[S:15][CH:14]=1.O>ClCCl>[Br:12][C:13]1[C:17]2[N:18]=[CH:19][N:20]=[C:6]([Cl:11])[C:7]=2[S:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1357437127-Bromothieno(3,2-d)pyrimidin-4-ol

Product 1

HCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylformamide (25.8 mL, 0.33 mol) and dichloromethane (150 mL) were added to a reactor. Oxalyl chloride (46.4 mL, 0.53 mol) diluted with dichloromethane (150 mL) at room temperature was added to the reactor for about 30 minutes. 7-bromothieno[3,2-d]pyrimidin-4(3H)-one (35 g, 0.15 mol) was added thereto, and then, the reaction solution was heated to reflux for 3 hours. The temperature of the reaction solution was lowered and water was carefully added thereto. The organic layer was separated, and the aqueous layer was subjected to extraction using dichloromethane. The extracted organic layer was dried over anhydrous sodium sulfate. The dried organic layer was filtered and distilled under reduced pressure, and dried with nitrogen gas to obtain the title compound (30.5 g, 85%).

Workup

  1. additionwas added to the reactor for about 30 minutes
  2. temperaturethe reaction solution was heated
  3. temperatureto reflux for 3 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was subjected to extraction
  6. dry with materialThe extracted organic layer was dried over anhydrous sodium sulfate
  7. filtrationThe dried organic layer was filtered
  8. distillationdistilled under reduced pressure
  9. customdried with nitrogen gas

Sources & evidence

ORD record
ord-e42a4dfe52444fa8a945854ba5058f7a
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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