Acetic Acid → HCID 178474467, compound

HRID 231297

Reaction equation

HRID 231297 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25]C(=O)C)=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>O>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178474468HCID 178474468, compound

Product 1

HCID 178474467HCID 178474467, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.95 g of 2-acetamido-4-hydroxy-6-[2-(4-acetoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 50 mL of water was added 1N aqueous sodium hydroxide until a homogenous solution was obtained. Acidification with acetic acid resulted in the formation of a yellow precipitate which was collected by filtration. The filter cake was washed sequentially with water, methanol, acetone and ether. The residual solid was recrystallized from DMF to give 0.65 g (77%) of the title compound, which can be alternatively named as 2-acetamido-6-(4-carboxystyryl)-5-deaza-4(3H)-pteridinone, as a microcrystalline yellow solid, mp >300° C.; NMR (TFA-d1) delta 2.5 (s, 3H), 6.85, 7.32 (AB q, 2H, J=12 Hz), 7.45, 8.18 (AB q, 4H, J=9 Hz), 8.65 (s, 1H), 9.02 (s, 1H); IR (Nujol) 3300-2200 (br), 1685, 1655, 1630, 1600, 1565 cm31 1. MS: Calc'd. for C18H14N4O4 : 350. Found: m/e 350 (base), 308.

Workup

  1. customwas obtained
  2. filtrationwas collected by filtration
  3. washThe filter cake was washed sequentially with water, methanol, acetone and ether
  4. customThe residual solid was recrystallized from DMF

Sources & evidence

ORD record
ord-26155caf68fc4b2cbf5e291c46bfa7cf
Source dataset
uspto-grants-1989_07
Patent number
US04845216

Linked notes

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