Phosphorus oxychloride → 5-Bromo-4-chloro-6-methylthieno[2,3-d]pyrimidine

HRID 2369414Notes

Reaction equation

HRID 2369414 reaction equation
[Br:1][C:2]1[C:10]2[C:9](O)=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[CH3:12].O=P(Cl)(Cl)[Cl:15]>>[Br:1][C:2]1[C:10]2[C:9]([Cl:15])=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[CH3:12]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178435035HCID 178435035, compound

Product 1

HCID 866733345-Bromo-4-chloro-6-methylthieno[2,3-d]pyrimidine

Conditions

Temperature
110 °C

Procedure

To a 25-mL round-bottom flask containing 5-bromo-6-methylthieno[2,3-d]pyrimidin-4-ol (100 mg, 0.41 mmol, 1.00 equiv) in POCl3 (10 mL) was stirred for 1 h at 110° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was then quenched with saturated aqueous sodium carbonate, extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. After concentrated under vacuum, this resulted 5-bromo-4-chloro-6-methylthieno[2,3-d]pyrimidine (79 mg, 73%) as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customThe residue was then quenched with saturated aqueous sodium carbonate
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentrated under vacuum

Sources & evidence

ORD record
ord-84339e94c1424ee49aad164fcb902167
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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