(Triphenylphosphoranylidene)acetonitrile → HCID 15516505, compound

HRID 1066054Notes

Reaction equation

HRID 1066054 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4](=[O:21])[C:3]=1[CH:22]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:31][C:32]#[N:33])C=CC=CC=1>C(#N)C>[NH2:33][C:32]1[CH:31]=[CH:22][C:3]2[C:4](=[O:21])[N:5]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:6](=[O:14])[N:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 15516504HCID 15516504, compound

Product 1

HCID 15516505HCID 15516505, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-amino-5-formyl-1,3-diphenyluracil (5.0 g, 16.3 mmol) and 2-(triphenylphosphoranylidene)acetonitrile (5.9 g, 19.6 mmol) in anhydrous acetonitrile (100 mL) was heated to reflux for 24 hours in an argon stream. The reaction mixture was allowed to cool and the solvent was evaporated therefrom in vacuo. The crude crystals separated out therefrom were recrystallized from benzene to give 7-amino-1,2,3,4-tetrahydro-1,3-diphenylpyrido[2,3-d]pyrimidine-2,4-dione (2.4 g) in a 45% yield.

Workup

  1. temperatureto reflux for 24 hours in an argon stream
  2. temperatureto cool
  3. customthe solvent was evaporated
  4. customThe crude crystals separated out
  5. customtherefrom were recrystallized from benzene

Sources & evidence

ORD record
ord-a0ab31f30a404821aa186828fffe0c87
Source dataset
uspto-grants-2001_06
Patent number
US06242452B1

Reaction notes

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