HCID 9968844, compound → Emivirine

HRID 1451210Notes

Reaction equation

HRID 1451210 reaction equation
C(O[CH:5]([C:12]1[N:17]([CH2:18][O:19][CH2:20][CH3:21])[C:16](=[O:22])[NH:15][C:14](=[O:23])[C:13]=1[CH:24]([CH3:26])[CH3:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C>O1CCOCC1.[Pd]>[CH2:5]([C:12]1[N:17]([CH2:18][O:19][CH2:20][CH3:21])[C:16](=[O:22])[NH:15][C:14](=[O:23])[C:13]=1[CH:24]([CH3:25])[CH3:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 9968844HCID 9968844, compound

Product 1

HCID 65013EmivirineYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-(α-acetoxybenzyl)-1-ethoxymethyl-5-isopropyluracil (13.3 g) in dioxane (53 ml) was added 5% Pd/C (0.66 g) and the mixture stirred for 4 hr at 50° C. under an atmosphere of hydrogen at ordinary pressure. After removal of Pd/C, the solvent was removed by distillation under reduced pressure. The residue was crystallized from ethanol (50 ml) in a refrigerator to yield 6-benzyl-1-ethoxymethyl-5-isopropyluracil (MKC-442) (10 g). M.p., 109°-110° C.

Workup

  1. customAfter removal of Pd/C
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was crystallized from ethanol (50 ml) in a refrigerator

Sources & evidence

ORD record
ord-39c954732ffd4041808f6c903f523066
Source dataset
uspto-grants-1997_02
Patent number
US05604209

Reaction notes

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