Ethanol → 4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenylamine

HRID 1010168Notes

Reaction equation

[Cl-].[NH4+].C(O)C.O.[N+:7]([C:10]1[CH:31]=[CH:30][C:13]([O:14][C:15]2[C:16]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)=[CH:12][CH:11]=1)([O-])=O>[Fe].O1CCCC1>[C:24]1([C:22]2[NH:21][C:17]3[N:18]=[CH:19][N:20]=[C:15]([O:14][C:13]4[CH:30]=[CH:31][C:10]([NH2:7])=[CH:11][CH:12]=4)[C:16]=3[CH:23]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 82.5 °C

Procedure

After adding 110 mg of iron powder, 220 mg of ammonium chloride, 10 ml of ethanol and 2 ml of water to 110 mg of 4-(4-nitrophenoxy)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine, the mixture was stirred at 80-85° C. for 2.5 hours. After returning the mixture to room temperature, 20 ml of tetrahydrofuran was added, and the mixture was stirred for 5 minutes and filtered with celite, after which 100 ml of ethyl acetate and 50 ml of water were added to the filtrate for liquid separation and extraction. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered with plug cotton and concentrated to dryness to obtain 90 mg of the title compound.

Workup

customto room temperature
stirringthe mixture was stirred for 5 minutes
filtrationfiltered with celite
additionafter which 100 ml of ethyl acetate and 50 ml of water were added to the filtrate for liquid separation and extraction
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered with plug cotton
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-e5cc357b8e8040808262a081fc36bc2c
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973160B2

Reaction notes

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