Phosphorus oxychloride → 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

HRID 2401533Notes

Reaction equation

HRID 2401533 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4](O)=[N:3][CH:2]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:4]1[C:5]2[CH:9]=[CH:8][NH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518057HCID 178518057, compound

Product 1

HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-Yield 42%

Procedure

To 7H-pyrrolo[2,3-d]pyrimidin-4-ol (0.425 g, 3.14 mmol) was added phosphorus oxychloride (4 ml). The mixture was heated at reflux for 90 minutes and then cooled to room temperature. The solution was poured onto cracked ice, and extracted with chloroform (3×50 ml) and ethyl acetate (100 ml). The extracts were then dried and concentrated, and the residue obtained triturated with hot ethyl acetate (200 ml) to yield the title compound (0.204 g, 42%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. additionThe solution was poured
  4. extractionextracted with chloroform (3×50 ml) and ethyl acetate (100 ml)
  5. customThe extracts were then dried
  6. concentrationconcentrated
  7. customthe residue obtained
  8. customtriturated with hot ethyl acetate (200 ml)

Sources & evidence

ORD record
ord-87c2897fee9944238254f212178e41cc
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

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