Water → HCID 178478305, compound

HRID 2042206Notes

Reaction equation

HRID 2042206 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.[BH4-].[Na+].O>O1CCCC1CCO>[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[NH:9][CH2:10][C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 183264227-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 178478305HCID 178478305, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

7-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine (1000 mg, 3.54 mmol) was dissolved in tetrahydrofuran-ethanol (1/1, 30 mL) and sodium borohydride (670 mg, 17.74 mmol) was added in several aliquots. The reaction mixture solution was cooled to room temperature and stirred for an hour. After adding water to terminate the reaction, the mixture solution was extracted with dichloromethane. The organic layer was washed with brine, dried with magnesium sulfate, and then concentrated. The yielded 7-bromo-2-chloro-3,4-dihydrothieno[3,2-d]pyrimidine (720 mg, 81% yield) was used without purification.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionthe mixture solution was extracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71d42031b2cf49ca990196de674b1c40
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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