Cyclohexanone → 6'-(pyridin-4-yl)-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2363930Notes

Reaction equation

[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[N:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:13](=[O:14])[NH:15][C:16]4([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.110 g, 0.500 mmol), cyclohexanone (0.245 g, 2.50 mmol), p-toluenesulfonic acid monohydrate (0.105 g, 0.550 mmol) and toluene (5.0 mL) was stirred for 1 h at 90° C. The mixture was poured into aqueous sodium hydrogen carbonate (30 mL). Extraction with ethyl acetate/tetrahydrofuran (2:1, 2×30 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was purified by column chromatography (12 g, silica, Combiflash, dichloromethane to 80:20 dichloromethane/methanol) to afford the title compound (0.053 g, 36%) as a yellow solid:

Workup

extractionExtraction with ethyl acetate/tetrahydrofuran (2:1, 2×30 mL)
dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
customgave an oil
customThe oil was purified by column chromatography (12 g, silica, Combiflash, dichloromethane to 80:20 dichloromethane/methanol)

Sources & evidence

ORD record: ord-bd603f2baa414cc783da7f502decb352
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

Loading…