Triethylamine → HCID 178464562, compound

HRID 1614306Notes

Reaction equation

HRID 1614306 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([Cl:12])[N:3]=1.[NH2:13][CH2:14][C:15]([NH2:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16].C(N(CC)CC)C.N1C=CC=NC=1>C(O)C>[ClH:12].[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH:13][CH2:14][C:15]([NH2:23])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])[N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9260PyrimidineHCID 1999232-Phenylpropane-1,2-diamineHCID 178418667HCID 178418667, compound

Product 1

HCID 178464562HCID 178464562, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

2-Amino-6-chloro-4-hydroxy-5-nitropyrimidine (0.626 g; 3.0 mmole) was dissolved in 130 ml of refluxing absolute ethanol and 0.45 g of 1,2-diamino-2-phenylpropane free-base (3.0 mmole) was added all at once dissolved in 8 ml of absolute ethanol. The mixture was stirred and maintained at reflux as a light yellow precipitate formed. Analysis by HPLC at 30 minutes showed a marked slowing of the condensation after a little over one-half of the reactants had been consumed. (Partisil SCX column (25×0.46 cm) eluted with 0.1M ammonium hydroxide made to pH 3.3 with formic acid/methanol, 3:2 v/v). Completion of the reaction to within 97% utilization of the diamine was accomplished by addition of 3.6 ml of 1M triethylamine in absolute ethanol (3.6 mmole) followed by 0.063 g of the above pyrimidine, the reaction being refluxed an additional hour. After being kept overnight at -15° C. the majority of the somewhat gelatinous product was collected by centrifugation, washed with 10 ml cold ethanol, and finally, twice with 30 ml each of ethyl ether. A second crop of equal purity was collected after allowing the mother liquor supernate to stand for an additional 5 days at -15° C., and similarly washed. These materials dried under vacuum in the presence of P2O5 gave 0.97 g (0.889+0.081) of the monohydrochloride salt for a yield of 95% based upon diamine.

Workup

  1. additionwas added
  2. temperaturemaintained
  3. temperatureat reflux as a light yellow precipitate
  4. customformed
  5. customa marked slowing of the condensation after a little over one-half of the reactants
  6. customhad been consumed
  7. wash(Partisil SCX column (25×0.46 cm) eluted with 0.1M ammonium hydroxide made to pH 3.3 with formic acid/methanol, 3:2 v/v)
  8. customCompletion of the reaction to within 97% utilization of the diamine
  9. temperaturethe reaction being refluxed an additional hour
  10. waitAfter being kept overnight at -15° C.
  11. customthe majority of the somewhat gelatinous product was collected by centrifugation
  12. washwashed with 10 ml cold ethanol
  13. customA second crop of equal purity was collected
  14. waitto stand for an additional 5 days at -15° C.
  15. washsimilarly washed
  16. dry with materialThese materials dried under vacuum in the presence of P2O5

Sources & evidence

ORD record
ord-050b8dc3716648a2b214034430ebec60
Source dataset
uspto-grants-1993_03
Patent number
US05196533

Reaction notes

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