Water → 4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

HRID 2114608Notes

Reaction equation

HRID 2114608 reaction equation
I[C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:3]=1.[OH2:17].[C]=O.CN([CH:23]=[O:24])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:11][C:9]1[C:10]2[C:2]([C:23]([OH:24])=[O:17])=[CH:3][N:4]([CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 195974344-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidineHCID 178418416HCID 178418416, compound

Product 1

HCID 717441504-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Starting material (1B, 10 g, 29 mmole) was taken in 500 mL DMF and 100 mL H2O together with palladium acetate (0.32 g, 1.4 mmole). The reaction mixture was stirred in a pressure reactor at 50° C. under 100 psi carbon monoxide for 6.5 h and room temperature for 16 h. The reaction mixture was then concentrated and residue triturated with 100 mL of 1:1 EtOAc/Ch2Cl2 followed by 50 mL CH2Cl2, The solid was collected after filtration and dried over P2O5 to furnish 21 g of an off-white solid. This solid was then triturated with a mixture of formic acid/H2O (21 mL/5 mL). The solid collected after filtration and drying over P2O5 furnished 6.5 g of 1 C (m/z 265.1, retention time 2.5 min. with HPLC method 1).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customresidue triturated with 100 mL of 1:1 EtOAc/Ch2Cl2
  3. customThe solid was collected
  4. filtrationafter filtration
  5. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-4d0403a8acca4df5a79722a04a2776f8
Source dataset
uspto-grants-2008_10
Patent number
US07435739B2

Reaction notes

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