Hydrochloric Acid → 2,4-Diamino-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine

HRID 231294Notes

Reaction equation

HRID 231294 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:27])[C:5]2[CH:11]=[C:10]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([O:22]C(C)(C)C)=[O:21])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1.Cl.CCOCC>[N+](C)([O-])=O>[NH2:1][C:2]1[N:3]=[C:4]([NH2:27])[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 538029442,4-Diamino-6-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Alternatively, 0.48 g of 2,4-diamino-6-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine was added to a saturated solution of hydrogen chloride in 20 mL of nitromethane at 0°. The reaction mixture quickly became viscous and turned a deep yellow color and after a few minutes of stirring, a granular solid formed. After 1 hour of stirring, 50 mL of ether were added and the precipitate was collected by filtration. The collected solid was dissolved in 50 mL of 10% aqueous sodium carbonate. Acidification with acetic acid then resulted in the separation of a yellow solid which was collected by filtration and dried under reduced pressure; yield 0.31 g (92%) of 2,4-diamino-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine; NMR (Me2SO-d6) delta 6.75 (s, 2H), 7.35, 7.85 (AB q, 4H, J=9 Hz), 8.38 (s, 2H); IR (Nujol) 3400-2300, 3380, 3150, 1700, 1650, 1630, 1590 cm-1.

Workup

  1. customa granular solid formed
  2. stirringAfter 1 hour of stirring
  3. filtrationthe precipitate was collected by filtration
  4. dissolutionThe collected solid was dissolved in 50 mL of 10% aqueous sodium carbonate
  5. customAcidification with acetic acid then resulted in the separation of a yellow solid which
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-0f361687775c4ab297508fa0dc627bfb
Source dataset
uspto-grants-1989_07
Patent number
US04845216

Reaction notes

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