4-Chloro-7-(3-chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine → 7-(3-Chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1869207Notes

Reaction equation

HRID 1869207 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12][CH2:13][Cl:14])[C:4]=2[N:5]=[CH:6][N:7]=1>CCOC(C)=O.[Pd]>[Cl:14][CH2:13][CH2:12][CH:11]([N:8]1[C:4]2[N:5]=[CH:6][N:7]=[CH:2][C:3]=2[CH:10]=[CH:9]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 579858984-Chloro-7-(3-chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579859167-(3-Chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidineYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-chloro-7-(3-chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine (150 mg, 0.5 mmol) and Pd/C (10%, 50% water, 150 mg) in EtOAc (50 mL) was stirred under H2 atmosphere (balloon pressure) for 4 h. The reaction mixture was filtered through a celite pad, and the filter cake was washed with EtOAc (20 mL). The filtrate was concentrated and purified via flash chromatography (hexane/EtOAc), affording 7-(3-Chloro-1-phenyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine (111 mg, 83% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe filter cake was washed with EtOAc (20 mL)
  3. concentrationThe filtrate was concentrated
  4. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-ed8ba392b71b4fe1a68d649f3cb0f90e
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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