Formamidine acetate → HCID 178514980, compound

HRID 1504073Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([CH2:12][CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])=[CH:5][C:6]=1[C:7]([O:9]CC)=O.C(O)(=O)C.[CH:29](N)=[NH:30]>CN(C)C=O>[OH:9][C:7]1[C:6]2[CH:5]=[C:4]([CH2:12][CH2:13][N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])[S:3][C:2]=2[N:1]=[CH:29][N:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 250-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was added a solution of ethyl 2-amino-5-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl]thiophene-3-carboxylate (3.4 g, 9.87 mmol, 1.00 equiv) and formamidine acetate (1.5 g, 14.41 mmol, 1.46 equiv) dissolved in 50 mL of N,N-dimethylformamide. This solution was heated at 100° C. for 12 hrs. The reaction was cooled to room temperature and quenched with water. The resulting mixture was extracted with 3×100 mL of ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to yield 1.76 g (55%) of 2-(2-[4-hydroxythieno[2,3-d]pyrimidin-6-yl]ethyl)-2,3-dihydro-1H-isoindole-1,3-dione as an off-white solid. MS (ES): m/z 326 (M+H)+.

Workup

customTo a 250-mL round-bottom flask, purged
temperaturemaintained with an inert atmosphere of nitrogen
temperatureThe reaction was cooled to room temperature
customquenched with water
extractionThe resulting mixture was extracted with 3×100 mL of ethyl acetate
washthe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-990e2f3ba3834721a55ee411f7eae133
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

Loading…