Sodium Methoxide → HCID 66802966, compound

HRID 515936Notes

Reaction equation

HRID 515936 reaction equation
[F:1][C@:2]1([CH3:18])[C@H:6]([OH:7])[C@@H:5]([CH2:8]I)[O:4][C@H:3]1[N:10]1[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]1=[O:17].C[O-].[Na+]>CO>[F:1][C@:2]1([CH3:18])[C@H:6]([OH:7])[C:5](=[CH2:8])[O:4][C@H:3]1[N:10]1[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]1=[O:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 66802642HCID 66802642, compound

Product 1

HCID 66802966HCID 66802966, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Chiral 1-((2R,3R,4R,5S)-3-fluoro-4-hydroxy-5-(iodomethyl)-3-methyl-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (8.2 g, 22 mmol) was dissolved in MeOH (100 mL) and NaOMe (3.73 g, 69 mmol) was added into it under nitrogen atmosphere, after addition, the mixture was heated to 65° C. and stirred under nitrogen atmosphere for 14 hrs, TLC showed that the SM was consumed, then the mixture cooled to r.t., IR-120 (H) ion exchange resin was added into it to adjust the pH to 8, filtered and removed solvent by reduced pressure, the crude product was purified by silica gel chromatography column (DCM:MeOH=15:1) to afford the title compound as a white solid (3.3 g, 59%).

Workup

  1. additionafter addition
  2. customwas consumed
  3. temperaturethe mixture cooled to r.t.
  4. additionIR-120 (H) ion exchange resin was added into it
  5. filtrationfiltered
  6. customremoved solvent by reduced pressure
  7. customthe crude product was purified by silica gel chromatography column (DCM:MeOH=15:1)

Sources & evidence

ORD record
ord-44bda6a4c0d24584b94ebf31204cfb3c
Source dataset
uspto-grants-2015_08
Patent number
US09108999B2

Reaction notes

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