Triphenylphosphine → HCID 67396730, compound

HRID 1990710Notes

Reaction equation

HRID 1990710 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:25]=[CH:24][N:23]=[C:22]([CH2:26][CH2:27][CH2:28]O)[CH:21]=2)=[CH:16][CH:15]=1.[O:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C.O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:25]=[CH:24][N:23]=[C:22]([CH2:26][CH2:27][CH2:28][N:32]3[C:33](=[O:35])[CH2:34][O:30][C:31]3=[O:36])[CH:21]=2)=[CH:18][CH:19]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 973892,4-OxazolidinedioneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67396768HCID 67396768, compound

Product 1

HCID 67396730HCID 67396730, compoundYield 79.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.4 ml of a 40% solution of diethyl azodicarboxylate (0.9 mmol) in toluene is added to a solution, cooled with an ice bath, of 0.111 g (0.44 mmol) of 3-[6-(4-chlorophenyl)pyrimidin-4-yl]propan-1-ol, prepared in stage 5.4., of 0.077 g (0.76 mmol) of 1,3-oxazolidine-2,4-dione and of 0.235 g (0.89 mmol) of triphenylphosphine in 4 ml of tetrahydrofuran. The mixture is subsequently stirred at ambient temperature overnight. It is taken up in a mixture of ethyl acetate and of water. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated. The residue is purified by chromatography on silica gel, elution being carried out with a 97/3 mixture of dichloromethane and of methanol, to produce 0.117 g (0.35 mmol) of product in the solid form.

Workup

  1. customprepared in stage 5.4
  2. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue is purified by chromatography on silica gel, elution
  6. additionbeing carried out with a 97/3 mixture of dichloromethane and of methanol

Sources & evidence

ORD record
ord-b3d365e1b1e54821b1d92847d8a57496
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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