Ethanol → HCID 67202157, compound

HRID 387728Notes

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 saline 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 saline in that order
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness under reduced pressure
washwashed with diethyl ether

Sources & evidence

ORD record: ord-f865032e60b3443691d20874c2996b59
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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