Benzyl Alcohol → HCID 18932925, compound

HRID 1656504Notes

Reaction equation

HRID 1656504 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8](C(O)=O)=[CH:7][N:6]=[C:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:2]=[CH2:3].C([N:22]([CH2:25]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[CH2:44]([OH:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O1CCOCC1>[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([NH:22][C:25]([O:51][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:34])=[CH:7][N:6]=[C:5]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18932912HCID 18932912, compound

Product 1

HCID 18932925HCID 18932925, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-allyl-2-phenylpyrimidin-6(1H)-one-5-carboxylic acid (30.2 g) and triethylamine (32.8 mL) in dioxane (390 mL) was added diphenylphosphoryl azide (25.6 mL), and the resulting solution was heated at 100° C. for 2 h. Benzyl alcohol (24.5 mL) was added and the resulting solution was heated at 100° C. for 12 h. The solution was cooled and the solvent evaporated. The resulting residue was dissolved in ethyl acetate, washed (saturated ammonium chloride, 1N sodium hydroxide, water), dried, and evaporated to give an oil which crystallized upon addition of ether to give a white solid. The solid was collected and washed with ether to provide 1-allyl-5-benzyloxycarbonylamino-2-phenylpyrimid-6(1H)-one (25.1 g); 300 MHz NMR: 8.93 (s,1), 8.45 (s,1), 7.43 (m,10), 5.75 (m,1), 5.18 (s,2), 5.08 (d,1), 4.82 (d,1), 4.46 (d,2).

Workup

  1. temperaturethe resulting solution was heated at 100° C. for 12 h
  2. temperatureThe solution was cooled
  3. customthe solvent evaporated
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. washwashed (saturated ammonium chloride, 1N sodium hydroxide, water)
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. customcrystallized upon addition of ether
  10. customto give a white solid
  11. customThe solid was collected
  12. washwashed with ether

Sources & evidence

ORD record
ord-3b669acd3f5e4de1866f5af5c0f12405
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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