2-Fluorophenol → HCID 178521642, compound

HRID 856891Notes

Reaction equation

HRID 856891 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[OH:5][CH2:6][C@@H:7]1[C@H:11]([OH:12])[C@H:10]([OH:13])[C@H:9]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3[NH:23][CH:24]2[CH2:28][CH2:27][O:26][CH2:25]2)[O:8]1.[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH2-:1][C:2]([CH3:4])=[O:3].[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:5][CH2:6][C@@H:7]1[C@H:11]([OH:12])[C@H:10]([OH:13])[C@H:9]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3[NH:23][CH:24]2[CH2:28][CH2:27][O:26][CH2:25]2)[O:8]1

Participants

6

Reactant 4

HCID 97072-FluorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178521062HCID 178521062, compound

Product 1

HCID 178521642HCID 178521642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4S,2R,3R,5R)-2-hydroxymethyl-5-[6-(tetrahydrofuran-3-ylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol acetonide (500 mg, 1.33 mmol), 2-fluorophenol (179.4 mg, 1.6 mmol), and triphenylphospine (418.3 mg, 1.6 mmol) in anhydrous tetrahydrofuran (20 mL), DIAD (diisopropylazodicarboxylate, 320 μL, 1.6 mmol) was added and heated to reflux for 16 hours. The reaction mixture was cooled to room temperature and the solvent evaporated. The residue was purified by column chromatography (eluting with ethyl acetate: hexane 50:50) to give (4S,2R,3R,5R)-2-(2-fluorophenoxy)methyl-5-[6-(tetrahydrofuran-3-ylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol acetonide as a pure white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. customthe solvent evaporated
  4. customThe residue was purified by column chromatography (eluting with ethyl acetate: hexane 50:50)

Sources & evidence

ORD record
ord-7fe8154a19754d86bbc55da9233d9778
Source dataset
uspto-grants-2006_12
Patent number
US07144871B2

Reaction notes

Loading…