Triphenylphosphine → HCID 18971823, compound

HRID 864353Notes

Reaction equation

HRID 864353 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:17]=[C:18]([CH:24]2[CH2:29][NH:28][C:27](=[O:30])[NH:26][CH2:25]2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]1([CH2:56][CH2:57][CH2:58][CH2:59]O)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>O1CCCC1.C(OCC)(=O)C>[C:50]1([CH2:56][CH2:57][CH2:58][CH2:59][O:15][C:16]2[CH:17]=[C:18]([CH:24]3[CH2:25][NH:26][C:27](=[O:30])[NH:28][CH2:29]3)[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 76889BenzenebutanolHCID 5363146Diisopropyl azodicarboxylateHCID 18971760HCID 18971760, compound

Product 1

HCID 18971823HCID 18971823, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropylazodicarboxylate (1.1 ml, 5.70 mmol, 1.2 eq) was added to a mixture of (1.06 g, 4.75 mmol, 1.0 eq) tetrahydro-5-(3-hydroxy-4-methoxyphenyl)-2(1H)-pyrimidinone, (1.37 g, 5.23 mmol, 1.1 eq) triphenylphosphine, and (714 mg, 4.75 mmol, 1.0 eq) 4-phenyl-1-butanol in 20 ml of anhydrous tetrahydrofuran. After heating to reflux for about 18 hours, the reaction mixture was cooled to room temperature, diluted with 350 ml ethyl acetate, washed twice with 1N NaOH, once with H2O, once with brine, dried over Na2SO4, and concentrated to yield an orange solid. Silica gel chromatography eluting with 4% CH3OH--CH2Cl2 yielded 527 mg of a white solid, which was recrystallized from ethyl acetate to afford 480 mg, 29%, of white needles. M.P.: 142°-143° C. Elemental Analysis Calc'd for C21H26N2O3 : Cal'd: C, 71.17; H, 7.40; N, 7.90. Found: C, 71.12; H, 7.32; N, 7.75.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for about 18 hours
  3. washwashed twice with 1N NaOH, once with H2O, once with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto yield an orange solid
  7. washSilica gel chromatography eluting with 4% CH3OH

Sources & evidence

ORD record
ord-fb30f391506f462c92aecb244fe97db1
Source dataset
uspto-grants-1996_10
Patent number
US05563143

Reaction notes

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