Ethanol → 5-(6-Phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylsulfanyl)-thiophen-2-ylamine

HRID 387772Notes

Reaction equation

[Cl-].[NH4+].CN(C)C=O.C(O)C.[N+:11]([C:14]1[S:18][C:17]([S:19][C:20]2[C:21]3[CH:28]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)=[CH:16][CH:15]=1)([O-])=O>[Fe].O1CCCC1.O>[C:29]1([C:27]2[NH:26][C:22]3[N:23]=[CH:24][N:25]=[C:20]([S:19][C:17]4[S:18][C:14]([NH2:11])=[CH:15][CH:16]=4)[C:21]=3[CH:28]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 90 °C

Procedure

After adding 543 mg of iron powder, 1.06 g of ammonium chloride, 10 ml of dimethylformamide, 20 ml of ethanol and 5 ml of water to the 4-(5-nitro-2-thiophenylsulfanyl)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine synthesized in Production Example 162-1, the mixture was stirred at 90° C. for 2 hours, 30 ml of tetrahydrofuran was added, and then the mixture was returned to room temperature and filtered with celite, and ethyl acetate and water were added to the filtrate for liquid separation and extraction. The organic layer was dried over anhydrous sodium sulfate, filtered with plug cotton and concentrated to dryness to obtain 435 mg of the title compound.

Workup

customsynthesized in Production Example 162-1
customwas returned to room temperature
filtrationfiltered with celite, and ethyl acetate and water
additionwere added to the filtrate for liquid separation and extraction
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered with plug cotton
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-58cc322241c74e3ca6b3357f838ec2eb
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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