Acetic Acid → 2-(((3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

HRID 1773441Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][C@H:13]2[C@@H:17]3[O:18][C:19]([CH3:22])([CH3:21])[O:20][C@@H:16]3[C@@H:15]([O:23][CH2:24][CH2:25][OH:26])[CH2:14]2)[C:3]=1[N+:27]([O-])=O.C(O)(=O)C>[Fe].O.C(O)C>[NH2:27][C:3]1[C:4]([NH:12][C@H:13]2[C@@H:17]3[O:18][C:19]([CH3:21])([CH3:22])[O:20][C@@H:16]3[C@@H:15]([O:23][CH2:24][CH2:25][OH:26])[CH2:14]2)=[N:5][C:6]([S:8][CH2:9][CH2:10][CH3:11])=[N:7][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 2-((3aR,4S,6R,6aS)-6-(6-chloro-5-nitro-2-(propylthio)pyrimidin-4-ylamino)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol (800 mg, 1.78 mmol, 1.00 equiv.), iron powder (800 mg, 14.29 mmol, 8.00 equiv.), acetic acid (860 mg, 14.33 mmol, 8.00 equiv.) and water/ethanol (10 mL) was stirred at about 60° C. for about 20 minutes in an oil bath. After the solids were removed by filtration, the resulting filtrate was extracted with dichloromethane (3×10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a yellow oil (780 mg; yield=93%). MS: m/z=419 (MH)+.

Workup

customAfter the solids were removed by filtration
extractionthe resulting filtrate was extracted with dichloromethane (3×10 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0d403971cd6b426e81adf9696d05e07e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255104B2

Reaction notes

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