Chloranil → 7-Bromo-2-chlorothieno(3,2-d)pyrimidine

HRID 2042207Notes

Reaction equation

HRID 2042207 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[NH:9][CH2:10][C:5]=2[S:4][CH:3]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1C=CC=CC=1>[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 178478305HCID 178478305, compound

Product 1

HCID 569657247-Bromo-2-chlorothieno(3,2-d)pyrimidineYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

7-Bromo-2-chloro-3,4-dihydrothieno[3,2-d]pyrimidine (750 mg, 3.0 mmol) and chloranil (740 mg, 3.0 mmol) were dissolved in benzene (30 mL) and stirred for 3 hours under reflux. The reaction mixture was cooled to room temperature and diluted with benzene (30 mL). The mixture solution was washed with 0.5 N sodium hydroxide (30 mL) solution and water. The organic layer was dried with magnesium sulfate and then concentrated. Purification of the resultant compound by chromatography (10% ethyl acetate/hexane) yielded the target compound (630 mg, 85% yield) as white solid.

Workup

  1. temperatureunder reflux
  2. washThe mixture solution was washed with 0.5 N sodium hydroxide (30 mL) solution and water
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the resultant compound by chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0e5109003dde4c38acdd7d0f007b09c5
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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