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

HRID 1010170Notes

Reaction equation

HRID 1010170 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].N1C(C)=CC=CC=1C.CN1CCCC1.Cl[C:27]1[C:28]2[CH:35]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:33][C:29]=2[N:30]=[CH:31][N:32]=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:27]1[C:28]2[CH:35]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:33][C:29]=2[N:30]=[CH:31][N:32]=1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 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-425d2b4e7466485da0e5c4bbf9bfc271
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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