Ethanol → HCID 67202157, compound

HRID 1433378Notes

Reaction equation

[Cl-].[NH4+].C(O)C.O.[N+:7]([C:10]1[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=1[O:12][C:13]1[C:14]2[C:21]([CH3:22])=[C:20]([CH3:23])[NH:19][C:15]=2[N:16]=[CH:17][N:18]=1)([O-])=O>[Fe].C(OCC)(=O)C.O1CCCC1>[NH2:7][C:10]1[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=1[O:12][C:13]1[C:14]2[C:21]([CH3:22])=[C:20]([CH3:23])[NH:19][C:15]=2[N:16]=[CH:17][N:18]=1

Participants

Conditions

Temperature: 78.5 °C

Procedure

After adding iron powder (0.1 g), ammonium chloride (0.2 g), ethanol (4 ml) and water (1 ml) to the 4-(nitrophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine (80 mg) synthesized by the intermediate synthesis method described above, the mixture was stirred at 75-82° C. for 1.5 hours. After returning the reaction system to room temperature and adding tetrahydrofuran (3 ml) and ethyl acetate (3 ml), the mixture was filtered with celite, the filtrate was subjected to liquid separation, and the organic layer was washed with water and saturated brine in that order, dried over sodium sulfate, concentrated to dryness under reduced pressure and washed with diethyl ether to obtain the title compound (22 mg).

Workup

customsynthesized by the intermediate synthesis method
customto room temperature
filtrationthe mixture was filtered with celite
customthe filtrate was subjected to liquid separation
washthe organic layer was washed with water and saturated brine in that order
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness under reduced pressure
washwashed with diethyl ether

Sources & evidence

ORD record: ord-17969e09ccfa473f86e4c213febb4ed1
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612092B2

Reaction notes

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