Potassium hydroxy sulfite → 2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

HRID 2189314Notes

Reaction equation

HRID 2189314 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH:11]=[O:12])[N:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:6]=2[N:7]=1.[OH:18]OS([O-])=O.[K+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([OH:18])=[O:12])[N:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 735546542-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde

Product 1

HCID 735546592-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acidYield 43.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (283 mg, 1.11 mmol) in DMF (3 mL) is added oxone (820 mg, 1.33 mmol) at room temperature. The mixture is stirred at room temperature for 5 h and is quenched with 20% Na2S2O3 aqueous solution. After stirring for 10 min, the reaction mixture is acidified with 1N HCl aqueous solution (pH=5). The mixture is extracted with dichloromethane, dried over Na2SO4 and concentrated in vacuo. The solid is filtered, washed with acetonitrile, and dried under vacuum to give 130 mg of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid as a pale brown solid.

Workup

  1. customis quenched with 20% Na2S2O3 aqueous solution
  2. stirringAfter stirring for 10 min
  3. extractionThe mixture is extracted with dichloromethane
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe solid is filtered
  7. washwashed with acetonitrile
  8. customdried under vacuum

Sources & evidence

ORD record
ord-6030276e7895451bb622049753c39402
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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