Selenium Dioxide → HCID 14267829, compound

HRID 1650894Notes

Reaction equation

HRID 1650894 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:17]=[N:16][C:9]2[NH:10][C:11](=[O:15])[NH:12][C:13](=[O:14])[C:8]=2[C:7]=1[CH3:18])(=[O:3])[CH3:2].[Se](=O)=[O:20]>C(O)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:17]=[N:16][C:9]2[NH:10][C:11](=[O:15])[NH:12][C:13](=[O:14])[C:8]=2[C:7]=1[CH:18]=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 14267828HCID 14267828, compound

Product 1

HCID 14267829HCID 14267829, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-acetoxymethyl-5-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (3.14 g, 12.5 mmol) and selenium dioxide (2.09 g, 18.9 mmol) in glacial acetic acid (100 mL) is heated at reflux for 20 hours, and then the mixture is filtered through a Celite pad while hot. The filtrate is concentrated in vacuo, and the residue is crystallized from methanol to give 6-acetoxymethyl-5-formylpyrido[2,3-d]-pyrimidine-2,4(1H, 3H)-dione (2.94 g, 86.6%), mp 263°-264° C. (decomposition). 1H NMR (Me2SO-d6) d 2.02 (3H, s, Ac), 5.03 (2H, s, CH2), 8.75 (1H, s, H-7, 10.49 (1H, s, CHO).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 hours
  3. filtrationthe mixture is filtered through a Celite pad while hot
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is crystallized from methanol

Sources & evidence

ORD record
ord-ebb910b12498484da82e01cf3876ce5a
Source dataset
uspto-grants-1990_05
Patent number
US04925939

Reaction notes

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