2-Fluorophenol → HCID 178521642, compound

HRID 641153Notes

Reaction equation

HRID 641153 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-7ceb7a0fc93e447eb15a330467fb12d8
Source dataset
uspto-grants-2010_04
Patent number
US07696181B2

Reaction notes

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