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

HRID 334151Notes

Reaction equation

HRID 334151 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 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione (10.38 g, 61.72 mmol) was dissolved in acetic acid (230 mL) and Bromine (11.13 mL, 216 mmol) was added. The reaction was heated at 80° C. for 3.5 h. Complete reaction was confirmed by LCMS. The reaction mixture was poured onto ice water slowly and filtered off the precipitate which was dried overnight under vacuum to give 7-bromothieno[3,2-d]pyrimidine-2,4(1H,3H)-dione (9.1 g, 60% yield)

Workup

  1. customComplete reaction
  2. additionThe reaction mixture was poured onto ice water slowly
  3. filtrationfiltered off the precipitate which
  4. customwas dried overnight under vacuum

Sources & evidence

ORD record
ord-2b62709c92634f6d93054bc037e3db69
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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