Sodium Carbonate → HCID 67747177, compound

HRID 1735124Notes

Reaction equation

HRID 1735124 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH2:9])[N:3]=1.Cl.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH2:19][NH:18][CH2:17][CH2:16]2.[C:25](=[O:28])([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Cl-].[Na+]>[ClH:1].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH2:19][N:18]([C:2]1[N:7]=[C:6]([N:18]3[CH2:17][CH2:16][C:15]4[C:20](=[CH:21][C:22]([O:28][CH3:25])=[C:13]([O:12][CH3:11])[CH:14]=4)[CH2:19]3)[N:5]=[C:4]([NH2:9])[N:3]=1)[CH2:17][CH2:16]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 136154,6-Dichloro-1,3,5-trazin-2-amineHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 67747177HCID 67747177, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

2,4-Dichloro-6-amino-1,3,5-triazine (5.13 g, 31.1 mM) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (14.72 g, 64 mM) were stirred in dioxane (40 mL) with sodium carbonate solution (2N, 65 mL) at reflux for 3 hr. The mixture was cooled and diluted with saturated sodium chloride solution (1000 mL) and extracted with methylene chloride (3×75 mL). Filtration through a cotton plug and concentration followed by evaporation from benzene (2×20 mL) provided a foam, 16.5 g. This material was combined with 7.8 g of crude product prepared analogously and recrystallized from chloroform/methanol to provide 13.85 g(61%). Recrystallization of free base (2.6 g) from hydrochloric acid/methanol (1N) provided a yellow powder, 2.17 g(78%), mp=259°-261° C.

Workup

  1. temperatureat reflux for 3 hr
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride (3×75 mL)
  4. filtrationFiltration
  5. concentrationthrough a cotton plug and concentration
  6. customfollowed by evaporation from benzene (2×20 mL)
  7. customprovided a foam, 16.5 g
  8. customprepared analogously
  9. customrecrystallized from chloroform/methanol
  10. customto provide 13.85 g(61%)
  11. customRecrystallization of free base (2.6 g) from hydrochloric acid/methanol (1N)
  12. customprovided a yellow powder, 2.17 g(78%), mp=259°-261° C.

Sources & evidence

ORD record
ord-5f9c225f59274bea934a310032bd7a3e
Source dataset
uspto-grants-1996_07
Patent number
US05536722

Reaction notes

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