Triphenylphosphine → 3-[4-Chloro-2-(1-methyl-2-propynyloxy)phenyl]-1-methyl-6-trifluoromethyluracil

HRID 366348Notes

Reaction equation

HRID 366348 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([OH:21])[CH:3]=1.[CH:22]#[C:23][CH:24](O)[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([O:21][CH:24]([CH3:25])[C:23]#[CH:22])[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 162393-Butyn-2-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 232891734-Chloro-2-hydroxyphenyl-1-methyl-6-trifluoromethyluracil

Product 1

HCID 232891833-[4-Chloro-2-(1-methyl-2-propynyloxy)phenyl]-1-methyl-6-trifluoromethyluracilYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.7 g (5.3 mmol) of 3-(4-chloro-2-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil, 0.63 g (9.0 mmol) of 1-butyn-3-ol and 1.57 g (6.0 mmol) of triphenylphosphine were dissolved in 100 ml of tetrahydrofuran, and 1.0 g (6.0 mmol) of diethyl azodicarboxylate was dropwise added thereto under cooling with ice. After stirring at room temperature for 1 hour, the solvent was distilled off. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.86 g (yield: 93.9%) of the desired product as white crystals. Melting point: 96-99° C.

Workup

  1. temperatureunder cooling with ice
  2. distillationthe solvent was distilled off
  3. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-011bc2d203404f63aea22967a21a57d0
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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