Hydrochloric Acid → (1S,2R,5S)-5-(8-Aminoimidazo[1,2-a]pyrazin-3-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol

HRID 2191378Notes

Reaction equation

Cl.CC1(C)[O:7][C@@H:6]2[C:8]([CH2:21][O:22]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:9][C@@H:10]([C:11]3[N:15]4[CH:16]=[CH:17][N:18]=[C:19]([NH2:20])[C:14]4=[N:13][CH:12]=3)[C@@H:5]2[O:4]1>CO>[NH2:20][C:19]1[C:14]2[N:15]([C:11]([C@H:10]3[C@H:5]([OH:4])[C@H:6]([OH:7])[C:8]([CH2:21][OH:22])=[CH:9]3)=[CH:12][N:13]=2)[CH:16]=[CH:17][N:18]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Concentrated HCl solution (0.6 mL) was added to 3-((3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine (1-9) (130 mg, 0.239 mmol, 1 equiv) in methanol (3 mL) and heated to 65° C. After 2 hours the mixture was cooled to 23° C. C and purified via reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) to afford (1S,2R,5S)-5-(8-aminoimidazo[1,2-a]pyrazin-3-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol (1-10) as an amber solid. 1H NMR (500 MHz, CD3OD) δ 8.04 (d, 1H, J=5.5 Hz), 7.62 (s, 1H), 7.24 (d, 1H, J=5.5 Hz), 5.93 (s, 1H), 4.51 (d, 1H, J=5.5 Hz), 4.31 (m, 2H), 4.23 (br m, 1H), 4.10 (t, 1H, J=5.5 Hz). LRMS m/z (M+H) 263.1 found, 263.1 required.

Workup

temperatureAfter 2 hours the mixture was cooled to 23° C
customC and purified via reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record: ord-3d5a33e9addf48b580a3225d1657c09f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329697B2

Reaction notes

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