Hydrochloric Acid → 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 1966392Notes

Reaction equation

HRID 1966392 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]=[CH:10]OCC)=[CH:4][N:3]=1.Cl>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:9]=[CH:10][NH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 573489732-Chloro-5-(2-ethoxy-vinyl)-pyrimidin-4-ylamine

Product 1

HCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Procedure

To a solution of 2-Chloro-5-(2-ethoxy-vinyl)-pyrimidin-4-ylamine (38.0 g, 0.19 mol) in ETOH (1000 ml) is added concentrated aqueous HCl (37%, 100 g, 1.00 mol) at rt. The reaction mixture is heated to reflux for 3 h and then evaporated to dryness under reduced pressure. Aqueous sodium carbonate solution (5%, 500 mL) is added to the residue, and the mixture is extracted with EtOAc (3×). The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The residue is recrystallized from hexane/ether (4/1, 250 ml) to give the title compound as an off-white solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 h
  3. customevaporated to dryness under reduced pressure
  4. additionAqueous sodium carbonate solution (5%, 500 mL) is added to the residue
  5. extractionthe mixture is extracted with EtOAc (3×)
  6. dry with materialThe combined organic layers are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is recrystallized from hexane/ether (4/1, 250 ml)

Sources & evidence

ORD record
ord-985a86b63a8b4a86bb6004c7bc352474
Source dataset
uspto-grants-2013_04
Patent number
US08420657B2

Reaction notes

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