Bromine → HCID 178435035, compound

HRID 2369413Notes

Reaction equation

HRID 2369413 reaction equation
[CH3:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([OH:10])[C:4]=2[CH:3]=1.[Br:12]Br>C(O)(=O)C>[Br:12][C:3]1[C:4]2[C:9]([OH:10])=[N:8][CH:7]=[N:6][C:5]=2[S:11][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 178422246HCID 178422246, compound

Product 1

HCID 178435035HCID 178435035, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-methylthieno[2,3-d]pyrimidin-4-ol (95 mg, 0.57 mmol, 1.00 equiv) in acetic acid (2 mL) was added Br2 (181 mg, 1.13 mmol, 2.00 equiv) and the resulting solution was stirred overnight at room temperature under nitrogen. After finished of the reaction, the reaction was then quenched with saturated aqueous NaHSO3 and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give the resulted 5-bromo-6-methylthieno[2,3-d]pyrimidin-4-ol (111 mg, 79%) as a yellow solid.

Workup

  1. customAfter finished of the reaction
  2. customthe reaction was then quenched with saturated aqueous NaHSO3
  3. extractionextracted with 3×50 mL of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dc958716a4f64052ad2770477fe19f3f
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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