Acetic Acid → HCID 178508854, compound

HRID 1651052Notes

Reaction equation

HRID 1651052 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](N)[C:5]2[CH:11]=[C:10]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1.C(O)(=[O:26])C>[OH-].[Na+]>[NH2:1][C:2]1[N:3]=[C:4]([OH:26])[C:5]2[CH:11]=[C:10]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 541209062,4-Diamino-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine

Product 1

HCID 178508854HCID 178508854, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 1.0 g of 2,4-diamino-6[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 30 mL of 1N aqueous sodium hydroxide was heated under reflux under nitrogen for 3 hours. The resulting homogenous orange solution was cooled to room temperature, acidified with 6 mL of glacial acetic acid, and the resulting yellow precipitate collected by filtration. The filter cake was washed successively with water, methanol, acetone and ether and was then dried under reduced pressure to give 0.88 g (88%) of the title compound as a microcrystalline yellow powder, mp>250° C.; NMR (TFA-dl delta 6.8, 7.25 (AB q, 2H, J=12 Hz), 7.45, 8.2 (AB q, 4H, J=9 Hz), 8.55 (s, 1H), 8.85 (s, 1H); IR (Nujol) 3500-2500 (br), 1670, 1625, 1600 cm-1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 3 hours
  3. filtrationthe resulting yellow precipitate collected by filtration
  4. washThe filter cake was washed successively with water, methanol, acetone and ether
  5. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-de7199aafbc24010885b0e7cd0b3f9d6
Source dataset
uspto-grants-1990_05
Patent number
US04927828

Reaction notes

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