Trifluoroacetic acid → 6-(2,3-Dihydroxy-propoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one oxime

HRID 1853304Notes

Reaction equation

C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH:19]([OH:22])[CH2:20][OH:21])[CH:15]=2)[O:10][C:9]([C:23]2[N:28]=[CH:27][N:26]3[CH:29]=[CH:30][CH:31]=[C:25]3[CH:24]=2)=[CH:8]1)(C)(C)C.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[OH:22][CH:19]([CH2:20][OH:21])[CH2:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:23]1[N:28]=[CH:27][N:26]3[CH:29]=[CH:30][CH:31]=[C:25]3[CH:24]=1)=[CH:8][C:7]2=[N:6][OH:5]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 6-(2,3-Dihydroxy-propoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime (example 86A) (100 mg, 0.236 mmol) in toluene (8 ml) was treated at 0° C. with trifluoro acetic acid (2 ml) and heated at 60° C. for 5.5 hours. The solution was concentrated under vacuum, the residue dissolved in ethyl acetate and washed successively with a saturated solution of sodium hydrogenocarbonate, brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel flash chromatography (gradient cyclohexane/ethyl acetate: 0-100% then ethyl acetate/methanol:90/10) to yield the title compound (38 mg, 44%) as a brown-yellow solid.

Workup

concentrationThe solution was concentrated under vacuum
dissolutionthe residue dissolved in ethyl acetate
washwashed successively with a saturated solution of sodium hydrogenocarbonate, brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel flash chromatography (gradient cyclohexane/ethyl acetate

Sources & evidence

ORD record: ord-bf5ed9a747594592b7b6d4322354d207
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962627B2

Reaction notes

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