4-Cyano-3-tetrahydrothiophenone → HCID 66980303, compound

HRID 1423312Notes

Reaction equation

O=[C:2]1[CH2:6][S:5][CH2:4][CH:3]1[C:7]#[N:8].[C:9]1([C:15]2[N:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][NH:24][C:25]=3[NH2:26])=[CH:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[C:9]1([C:15]2[N:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][N:24]4[C:7]([NH2:8])=[C:3]5[CH2:4][S:5][CH2:6][C:2]5=[N:26][C:25]=34)=[CH:17][CH:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 4-oxotetrahydrothiophene-3-carbonitrile (77.6 mg, 0.61 mmol) and 4-(6-phenylpyridin-3-yl)-1H-pyrazol-5-amine (144 mg, 0.61 mmol) in toluene (10 mL) was heated at 115° C. overnight. Concentration and purification with prep-LC provided 3-(6-phenylpyridin-3-yl)-5,7-dihydropyrazolo[1,5-a]thieno[3,4-d]pyrimidin-8-amine: LCMS tR=1.48 Min (5 min run, UV254mn), Mass calculated for, M+345.1, observed LC/MS m/z 346.1 (M+H).

Workup

concentrationConcentration and purification

Sources & evidence

ORD record: ord-007ae8e298f2460e8c78d3fd04f0b6b0
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927562B2

Reaction notes

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