Hydrochloric Acid → 2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde

HRID 2189313Notes

Reaction equation

HRID 2189313 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]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:6]=2[N:7]=1.Cl.[OH-].[Na+].C([O-])(O)=O.[Na+]>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]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 580158842-Chloro-6-diethoxymethyl-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 735546542-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehydeYield 107.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-6-diethoxymethyl-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine (67 mg, 0.2 mmol) in 1,4-dioxane (0.7 mL) is added conc. HCl (0.2 mL) at ambient temperature. The reaction mixture is stirred for 30 min, then neutralized with 2N NaOH aqueous solution and saturated NaHCO3 aqueous solution. The mixture is extracted with EtOAc. The extracts are washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give 54 mg of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde as a yellow solid. The crude product is used as it is.

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. washThe extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ce84091f3a84438bc990e763b50a8e4
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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