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1-Methylpyrrolidine → 4-(3-fluoro-4-nitrophenoxy)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 853305
Notes
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Reaction equation

HRID 853305 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].CN1CCCC1.Cl[C:19]1[C:20]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][C:21]=2[N:22]=[CH:23][N:24]=1>O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][C:19]1[C:20]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][C:21]=2[N:22]=[CH:23][N:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 84541-MethylpyrrolidineHCID 5209483-Fluoro-4-nitrophenolHCID 224844424-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 589311924-(3-fluoro-4-nitrophenoxy)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidineYield 20.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

After adding 328 mg of 3-fluoro-4-nitrophenol, 0.22 ml of 2, 6-lutidine and 0.9 ml of N-methylpyrrolidine to 360 mg of the 4-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine described in WO97/02266 and PCT/EP96/02728 and stirring the mixture overnight at 130° C., it was returned to room temperature, water was added, the precipitated solid was filtered out and washed with water and diethyl ether, and the collected solid was dried to obtain 112 mg of the title compound.

Workup

  1. customwas returned to room temperature
  2. filtrationthe precipitated solid was filtered out
  3. washwashed with water and diethyl ether
  4. customthe collected solid was dried

Sources & evidence

ORD record
ord-0c1b1a2f44584ec8a5c11c3f07ab9cef
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253286B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes