Hydrochloric Acid → HCID 136344413, compound

HRID 1022453Notes

Reaction equation

HRID 1022453 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([CH:11]3[CH2:13][CH2:12]3)[C:6]=2[N:7]=1.[OH-:15].[K+].Cl>O>[Cl:1][C:2]1[NH:3][C:4](=[O:15])[C:5]2[CH:10]=[CH:9][N:8]([CH:11]3[CH2:13][CH2:12]3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 583988902,4-Dichloro-7-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 136344413HCID 136344413, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-dichloro-7-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidine (68 mg, 298 μmol) in a 2N aqueous potassium hydroxide solution (1.67 ml, 3.34 mmol) was heated to 100° C. overnight. At this time, the reaction was cooled to room temperature. The reaction was diluted with water (−50 mL) and then neutralized by the addition of a 2N aqueous hydrochloric acid solution. The product was extracted into a 10% methanol/methylene chloride solution (3×25 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-chloro-7-cyclopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a light yellow solid (59.9 mg, 95.8%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.78-1.17 (m, 4H) 3.50 (s, 1H) 6.42 (d, J=3.39 Hz, 1H) 7.07 (br. s., 1H) 12.87 (br. s., 1H). LC-MS calcd. for C9H9ClN3O [(M+H)+] 210, obsd. 209.9.

Workup

  1. temperatureAt this time, the reaction was cooled to room temperature
  2. extractionThe product was extracted into a 10% methanol/methylene chloride solution (3×25 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64fc83386f0146d9ab8e275c1eb113d9
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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