Bromine → 7-Bromothieno(3,2-d)pyrimidin-4-ol

HRID 1181269Notes

Reaction equation

HRID 1181269 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4](=[O:10])[NH:3][CH:2]=1.[Br:11]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:11][C:7]1[C:6]2[N:1]=[CH:2][NH:3][C:4](=[O:10])[C:5]=2[S:9][CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 1357437127-Bromothieno(3,2-d)pyrimidin-4-olYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3H-thieno[3,2-d]pyrimid-4-one (82, 0.98 g, 6.4 mmol) in acetic acid (3.4 mL) was added a solution of bromine (1 mL) in acetic acid (3 mL). The reaction mixture was heated at reflux for 8 hours. The resulting suspension was allowed to cool to room temperature and then poured into a saturated aqueous solution of sodium bicarbonate to neutralize. The solid product was collected by vacuum filtration to give 7-bromo-3H-thieno[3,2-d]pyrimid-4-one (0.94 g, 64% yield) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 8 hours
  3. filtrationThe solid product was collected by vacuum filtration

Sources & evidence

ORD record
ord-d23b7f0a783949f382637a38916cac13
Source dataset
uspto-grants-2007_10
Patent number
US07285556B2

Reaction notes

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