Hydrochloric Acid → 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde

HRID 2359568Notes

Reaction equation

HRID 2359568 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH:11](OCC)[O:12]CC)[N:8]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:6]=2[N:7]=1.Cl.O.CCCCCCC.C(OCC)(=O)C>O1CCOCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH:11]=[O:12])[N:8]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21899848Ethylacetate heptaneHCID 58315449HCID 58315449, compound

Product 1

HCID 583154052-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehydeYield 82.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-7-cyclopentyl-6-diethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine (4.26 g, 13 mmol) in dioxane is added concentrated HCl. After reaction is completed within 10 min, water is added and then extracted with ethyl acetate. Solvent is removed to give a brown color crude product. Column is run using heptane/ethyl acetate (6:4) to give 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (2.69 g, 82%). MS (ESI) m/z 350.4 (M+H)+

Workup

  1. customAfter reaction
  2. extractionextracted with ethyl acetate
  3. customSolvent is removed
  4. customto give a brown color crude product

Sources & evidence

ORD record
ord-a91d8c709b4c4e77a72e8bb6c22f7027
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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