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

HRID 2426278Notes

Reaction equation

HRID 2426278 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>C(O)(C)C>[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

4

Reactant 2

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

Product 1

HCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidineYield 100.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A 500 mL round bottomed flask was charged with 2-Chloro-5-(2-ethoxyvinyl)-pyrimidin-4-ylamine 2 (4.4 g, 20 mmol). Isopropanol (200 mL) is added followed by 25 mL of concentrated hydrochloric acid. The solution is heated to 90° C. and stirred for two hours. After cooling to room temperature, the solution is concentrated under reduced pressure then basified to pH 9 with saturated aqueous NaHCO3. The aqueous layer is extracted with ethyl acetate, and the organic extracts are combined and washed with saturated aqueous NaHCO3 and brine. The organic extracts are dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by short-filtration (SiO2, Hexanes:Ethyl acetate/1:1) gives 3 (3.1 g, 92%) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution is concentrated under reduced pressure
  3. extractionThe aqueous layer is extracted with ethyl acetate
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialThe organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification
  9. filtrationby short-filtration (SiO2, Hexanes:Ethyl acetate/1:1)

Sources & evidence

ORD record
ord-a31481d417a94f45a182da3cc9f0966a
Source dataset
uspto-grants-2011_06
Patent number
US07968557B2

Reaction notes

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