Phosphorus oxychloride → HCID 20068700, compound

HRID 982143Notes

Reaction equation

HRID 982143 reaction equation
[CH:1]1([CH:4]2[NH:9][C:8]3=[CH:10][S:11][CH:12]=[C:7]3[C:6](O)=[N:5]2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:6]1[C:7]2[C:8](=[CH:10][S:11][CH:12]=2)[NH:9][CH:4]([CH:1]2[CH2:3][CH2:2]2)[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517400HCID 178517400, compound

Product 1

HCID 20068700HCID 20068700, compound

Procedure

2-Cyclopropyl-4-hydroxydihydrothieno[3,4-d]pyrimidine (2.4 g, 0.0123M) was refluxed in phosphorus oxychloride (40 ml) for 11/2 hours. The mixture was cooled, concentrated under vacuum, the residue dissolved in chloroform, poured over ice, and basified with ammonia. The layers were separated and the organic solution dried (MgSO4) and concentrated. The residue, chromatographed on silica eluting with ethyl acetate/hexane, (1/6) gave 2.2 g of product, m.p. 86.5°-88.5° C. the structure of which was confirmed by NMR.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under vacuum
  3. dissolutionthe residue dissolved in chloroform
  4. additionpoured over ice
  5. customThe layers were separated
  6. dry with materialthe organic solution dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue, chromatographed on silica eluting with ethyl acetate/hexane, (1/6)

Sources & evidence

ORD record
ord-6513f736cacc415dbaf268b3779f056c
Source dataset
uspto-grants-1991_02
Patent number
US04994464

Reaction notes

Loading…