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

HRID 853305Notes

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

Participants

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

customwas returned to room temperature
filtrationthe precipitated solid was filtered out
washwashed with water and diethyl ether
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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