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

HRID 2363967Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([NH2:17])=[O:16])[CH3:2].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[C:4]2[CH:8]=[C:7]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)[S:6][C:5]=2[C:15](=[O:16])[NH:17][C:18]21[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.100 g, 0.400 mmol), cyclohexanone (2.0 mL, 1.9 g, 19 mmol), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred overnight at 100° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate (100 mL, 30 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave a solid. The solid was triturated with DMF/dichloromethane, then the precipitate was collected by filtration to afford the title compound (0.0738 g, 56%) as a yellow solid:

Workup

extractionExtraction with ethyl acetate (100 mL, 30 mL)
dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
customgave a solid
customThe solid was triturated with DMF/dichloromethane
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-28b5cbcd86784300b589e1902b10cc54
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

Loading…