Sodium Iodide → HCID 18366184, compound

HRID 342385Notes

Reaction equation

HRID 342385 reaction equation
[I-].[Na+].Cl[Si:4]([CH3:7])([CH3:6])[CH3:5].[NH2:8][C:9]1[N:17]=[C:16]2[N:11]([C:12]([O:19][CH3:20])=[N:13][CH:14]=[C:15]2[Cl:18])[N:10]=1.C(N(CC)CC)C>C(#N)C.C(OCC)C>[CH3:5][Si:4]([CH3:7])([CH3:6])[NH:8][C:9]1[N:17]=[C:16]2[N:11]([C:12]([O:19][CH3:20])=[N:13][CH:14]=[C:15]2[Cl:18])[N:10]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 187699738-Chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

Product 1

HCID 18366184HCID 18366184, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 12.7 g (85 mmol) of sodium iodide in 425 mL of dry acetonitrile was prepared under nitrogen in a predried 2 L flask and to this mixture 9.25 g (10.8 mL, 85 mmol) of chlorotrimethylsilane was added by means of a syringe at ambient temperature with stirring. After 10 min, 17.0 g (85 mmol) of 2-amino-8-chloro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine and 8.62 g (11.9 mL, 85 mmol) of triethylamine were added with stirring. The mixture was allowed to react for 12 hours at ambient temperature with stirring and was then diluted with 500 mL of dry diethyl ether. The salts that precipitated were removed by filtration on a dry scintered glass filter and the filtrate was concentrated by evaporation under reduced pressure. The residue was diluted with another 500 mL of dry diethyl ether the salt removal procedure was repeated. The title compound was obtained as the solid residue and amounted to 19.5 g (84 percent of theory).

Workup

  1. additionwas added by means of a syringe at ambient temperature
  2. stirringwith stirring
  3. customto react for 12 hours at ambient temperature
  4. stirringwith stirring
  5. customThe salts that precipitated
  6. customwere removed by filtration on a dry scintered glass
  7. filtrationfilter
  8. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  9. additionThe residue was diluted with another 500 mL of dry diethyl ether
  10. customthe salt removal procedure

Sources & evidence

ORD record
ord-004838c2ffda40e2a1e55d1b0fa2a86e
Source dataset
uspto-grants-1999_01
Patent number
US05858924

Reaction notes

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