(Triphenylphosphoranylidene)acetonitrile → Pyrido(2,3-d)pyrimidine-2,4(1H,3H)-dione, 7-amino-1,3-dimethyl-

HRID 1382722Notes

Reaction equation

HRID 1382722 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]=O.[C:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:15]>C(#N)C>[NH2:15][C:14]1[CH:16]=[CH:12][C:3]2[C:4](=[O:11])[N:5]([CH3:10])[C:6](=[O:9])[N:7]([CH3:8])[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 2946886-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Product 1

HCID 3040482Pyrido(2,3-d)pyrimidine-2,4(1H,3H)-dione, 7-amino-1,3-dimethyl-Yield 39.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.18 g of 6-amino-5-formyl-1,3-dimethyluracil and 0.45 g of cyanomethylenetriphenylphosphorane were added to 20 ml of dried acetonitrile. The solution was heated under reflux for 12 hr in a stream of argon. After cooling, the precipitated crystal was separated by filtration to give 0.08 g of 7-amino-1,3-dimethylpyrido[2,3-d]pyrimidine-2,4-dione (Compound 15).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 12 hr in a stream of argon
  3. temperatureAfter cooling
  4. customthe precipitated crystal was separated by filtration

Sources & evidence

ORD record
ord-f26206adcbe9470db5e0e32f33788dcc
Source dataset
uspto-grants-1989_02
Patent number
US04808587

Reaction notes

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