Guanidine Hydrochloride → 2,4,6-Triamino-5-[3-(naphth-1-yl)propyl]pyrimidine

HRID 440967Notes

Reaction equation

HRID 440967 reaction equation
[O-]CC.[Na+].[Na].Cl.[NH2:7][C:8]([NH2:10])=[NH:9].[C:11]([CH:13]([CH2:16][CH2:17][CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[C:14]#[N:15])#[N:12]>C(O)C>[NH2:9][C:8]1[N:10]=[C:14]([NH2:15])[C:13]([CH2:16][CH2:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)=[C:11]([NH2:12])[N:7]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 199555442-Cyano-5-(naphth-1-yl)pentanenitrile

Product 1

HCID 199555012,4,6-Triamino-5-[3-(naphth-1-yl)propyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium ethoxide, prepared from 0.04 gram (0.002 mole) of sodium metal in 50 mL of ethanol, was stirred, and 0.2 gram (0.002 mole) of guanidine hydrochloride was added in one portion. The reaction mixture was stirred for 15 minutes and filtered to remove a precipitate. The filtrate was stirred, and 0.4 gram (0.002 mole) of 2-cyano-5-(naphth-1-yl)pentanenitrile was added in one portion. Upon completion of addition, the reaction mixture was heated at reflux for about 16 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was triturated with warm water, yielding, when dried, 0.4 gram of 2,4,6-triamino-5-[3-(naphth-1-yl)propyl]-pyrimidine, mp 181°-183° C., (dec.). The NMR spectrum was consistent with the proposed structure.

Workup

  1. stirringThe reaction mixture was stirred for 15 minutes
  2. filtrationfiltered
  3. customto remove a precipitate
  4. stirringThe filtrate was stirred
  5. additionUpon completion of addition
  6. temperaturethe reaction mixture was heated
  7. temperatureat reflux for about 16 hours
  8. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  9. customThe residue was triturated with warm water
  10. customyielding
  11. customwhen dried

Sources & evidence

ORD record
ord-884a174be3224f5c9e9481173a64c3ec
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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