Ethanol → HCID 58931023, compound

HRID 387774Notes

Reaction equation

[Cl-].[NH4+].C(O)C.O.[CH2:7]([O:9][C:10]([C:12]1[NH:30][C:15]2[N:16]=[CH:17][N:18]=[C:19]([O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[C:14]=2[CH:13]=1)=[O:11])[CH3:8]>[Fe].O1CCCC1>[CH2:7]([O:9][C:10]([C:12]1[NH:30][C:15]2[N:16]=[CH:17][N:18]=[C:19]([O:20][C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[C:14]=2[CH:13]=1)=[O:11])[CH3:8]

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 4-(4-nitrophenoxy)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester, 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, the mixture was stirred for 5 minutes and filtered with celite, and 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 saline, 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, and 100 ml of ethyl acetate and 50 ml of water
additionwere added to the filtrate for liquid separation and extraction
washThe organic layer was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered with plug cotton
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-90dd09bf1ef3421ba1266eaebc164862
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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