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

HRID 1962141Notes

Reaction equation

HRID 1962141 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. Alter 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. customreaction
  2. extractionextracted with ethyl acetate
  3. customSolvent is removed
  4. customto give a brown color crude product

Sources & evidence

ORD record
ord-ff2e02da311f4065b2b0f5e1f55ace25
Source dataset
uspto-grants-2013_04
Patent number
US08415355B2

Reaction notes

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