Trifluoroacetic acid → HCID 58317598, compound

HRID 2092728Notes

Reaction equation

FC(F)(F)C(O)=O.COC1C=C(OC)C=CC=1C[N:13]1[C:18]([CH2:19][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])=[C:17]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:16](=[O:36])[NH:15][C:14]1=[O:37]>>[O:29]=[C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:30])[N:20]1[CH2:19][C:18]1[NH:13][C:14](=[O:37])[NH:15][C:16](=[O:36])[C:17]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58317531HCID 58317531, compound

Product 1

HCID 58317598HCID 58317598, compoundYield 132.5%

Conditions

Temperature: 0 °C

Procedure

To trifluoroacetic acid (2 mL, 26.0 mmol) was added ethyl 1-(2,4-dimethoxybenzyl)-6-((1,3-dioxoisoindolin-2-yl)methyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (198.9 mg, 0.403 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h, then at RT for 6 h. The mixture was concentrated under reduced pressure, and the residue was washed with IPE (5 mL) to give the title compound (183.3 mg). 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.2 Hz, 3H), 4.45 (q, J=7.2 Hz, 2H), 4.98 (s, 2H), 7.78-7.81 (m, 2H), 7.91-7.93 (m, 2H), 8.19 (br s, 1H), 8.96 (br s, 1H).

Workup

waitat RT for 6 h
concentrationThe mixture was concentrated under reduced pressure
washthe residue was washed with IPE (5 mL)

Sources & evidence

ORD record: ord-f7cdc4151a13413cac7d09b11a2fc485
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440689B2

Reaction notes

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