Acetic Acid → HCID 178508854, compound

HRID 1788707Notes

Reaction equation

HRID 1788707 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 homogeneous 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, which can be alternatively named as either 6-[2-(4-carboxyphenyl)ethenyl]-5-deazapterin or 6-(4-carboxystyryl)-5-deazapterin, as a microcrystalline yellow powder, mp >250° C.; NMR (TFA-d1 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-4e81c798b862450ba203c6d390f30e54
Source dataset
uspto-grants-1987_08
Patent number
US04684653

Reaction notes

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