Guanidine Hydrochloride → HCID 178450672, compound

HRID 1199810Notes

Reaction equation

HRID 1199810 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].[C:7]([O:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]2[CH:23]=[C:24]([C:29](OC)=[O:30])[C:25](Cl)=[N:26][CH:27]=2)=[CH:16][CH:15]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C(O)(C)(C)C.C(O)C>[NH2:5][C:4]1[N:6]=[C:29]([OH:30])[C:24]2[CH:23]=[C:22]([C:21]#[C:20][C:17]3[CH:18]=[CH:19][C:14]([C:12]([O:11][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:13])=[CH:15][CH:16]=3)[CH:27]=[N:26][C:25]=2[N:3]=1

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 14750211HCID 14750211, compound

Product 1

HCID 178450672HCID 178450672, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution containing 0.11 g of sodium in 30 ml of anhydrous tert.-butanol is added 0.45 g of guanidine hydrochloride. After stirring the mixture at room temperature for 15 minutes, 0.35 g of methyl 5-(4-tert.-butoxycarbonylphenyl)ethynyl-2-chloro-3-pyridinecarboxylate is added in one portion. The mixture is heated under reflux under nitrogen for 4 hours, cooled, diluted with ethanol, and the solvent removed under reduced pressure. The residue is dissolved in water and filtered to remove a small amount of insoluble material. The filtrate is acidified with a 3N hydrochloric acid solution and the precipitate that forms is collected by filtration, washed with water, and dried under reduced pressure to give 0.15 g (44%) of 2-amino-4-hydroxy-6-(4-tert.-butoxycarbonylphenylethynyl)pyrido[2,3-d]pyrimidine as a pale yellowish solid: m.p. >260° C.; NMR (DMSO-d6, 80 MHz) delta 1.55 (s, 9H), 7.71 (d, 2H, J=8.6 Hz), 7.96 (d, 2H, J= 8.6 Hz), 8.36 (d, 1H, J=2.5 Hz), 8.73 (d, 1H, J=2.5 Hz).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux under nitrogen for 4 hours
  3. temperaturecooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue is dissolved in water
  6. filtrationfiltered
  7. customto remove a small amount of insoluble material
  8. filtrationthe precipitate that forms is collected by filtration
  9. washwashed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-22110f71a67945d9847ba0f76fe947a5
Source dataset
uspto-grants-1990_02
Patent number
US04902796

Reaction notes

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