Phosphorus oxychloride → 7-Bromo-4-chlorothieno[3,2-d]pyrimidine

HRID 1518347Notes

Reaction equation

HRID 1518347 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[S:4][CH:3]=1.O=P(Cl)(Cl)[Cl:14]>>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([Cl:14])[C:5]=2[S:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 1357437127-Bromothieno(3,2-d)pyrimidin-4-ol

Product 1

HCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidine

Procedure

7-Bromothieno[3,2-d]pyrimidin-4(3H)-one (0.9 g, 3.89 mmol) in POCl3 was heated under reflux for 2 hours and excess of POCl3 was removed under reduced pressure. The residue was partitioned between water and EtOAc. The organic layer was separated, and the aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated to give 0.91 g of the compound 65A: 1H NMR (DMSO-d6): δ 9.15 (s, 1H), 8.78 (s, 1H). ESI (+)/MS: 248 (M−H)+.

Workup

  1. customwas removed under reduced pressure
  2. customThe residue was partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f9cd15444cde4b9f92220abf6f1ea0fb
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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