Phosphorus oxychloride → 4-Chloro-2-ethylthieno(3,2-d)pyrimidine

HRID 982141Notes

Reaction equation

HRID 982141 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5](O)[C:6]2[S:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:2].P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:5]1[C:6]2[S:11][CH:10]=[CH:9][C:7]=2[N:8]=[C:3]([CH2:1][CH3:2])[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178437764HCID 178437764, compound

Product 1

HCID 107031404-Chloro-2-ethylthieno(3,2-d)pyrimidine

Procedure

2-Ethyl-4-hydroxythieno[3,2-d]pyrimidine (0.6725 g, 0.00373M) was refluxed with phosphorus oxychloride (20 ml) for 2 hours. The reaction mixture was cooled, concentrated under vacuum, the residue dissolved in methylene chloride, poured over ice and water and basified with ammonia. The layers were separated and the aqueous layer extracted with ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under vacuum to obtain the product, 0.65 g, as a tan solid, m.p. 46°-48° C. the structure of which was confirmed by NMR.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under vacuum
  3. dissolutionthe residue dissolved in methylene chloride
  4. additionpoured over ice and water and basified with ammonia
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with ether
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under vacuum
  10. customto obtain the product, 0.65 g

Sources & evidence

ORD record
ord-86d31da125e64ec195f438167ae30ff0
Source dataset
uspto-grants-1991_02
Patent number
US04994464

Reaction notes

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