Bromine → 7-Bromothieno[3,2-d]pyrimidine-2,4(1h,3h)-dione

HRID 2042205Notes

Reaction equation

HRID 2042205 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4](=[O:10])[NH:3][C:2]1=[O:11].[Br:12]Br>C(O)(=O)C>[Br:12][C:7]1[C:6]2[NH:1][C:2](=[O:11])[NH:3][C:4](=[O:10])[C:5]=2[S:9][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 7059273Thieno(3,2-d)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 183264277-Bromothieno[3,2-d]pyrimidine-2,4(1h,3h)-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution in which thieno[3,2-d]pyrimidin-2,4(1H,3H)-dione (5.0 g, 29.5 mmol) was dissolved in glacial acetic acid (200 mL), bromine (4.55 mL, 89.0 mmol) was added. The reaction mixture solution was stirred at 110° C. for 30 hours, cooled to room temperature, and then slowly added to ice water (400 mL). Drying of thus prepared solid followed by filtration, washing several times with water and drying yielded the target compound 7-bromothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione (6.5 g, 90% yield).

Workup

  1. temperaturecooled to room temperature
  2. customDrying of thus prepared solid
  3. filtrationfollowed by filtration
  4. washwashing several times with water
  5. customdrying

Sources & evidence

ORD record
ord-03a6b29ce4984045820cb10158bf6844
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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