Ammonium formate → HCID 23371649, compound

HRID 1729199Notes

Reaction equation

HRID 1729199 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)[N:5]=[C:4]([NH:17][CH3:18])[N:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[N:8]1([C:6]2[N:5]=[C:4]([NH:17][CH3:18])[N:3]=[CH:2][N:7]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 23371653HCID 23371653, compound

Product 1

HCID 23371649HCID 23371649, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-4-indolin-1-yl-6-methylamino-1,3,5-triazine (5.0 g, 19.1 mM), ammonium formate (6.02 g, 95.6 mM), 10% w/w palladium on charcoal (1.0 g) and methanol (100 ml) was heated at 50° C., under argon, for 6 hours. The mixture was cooled, basified, and filtered. The solid collected by filtration was heated at reflux with ethanol, and the mixture refiltered. The filtrates were combined and the solvent evaporated. The residual solid was washed with water and then purified by flash column chromatography (silica, Merck 9385), eluting with ethyl acetate/hexane (1:3). This gave a solid which was recrystallised from ethyl acetate. There was thus obtained 2-(indolin-1-yl)-4-methylamino-1,3,5-triazine (1.7 g, 39% yield); m.p. 185°-187° C.: micro analysis, found: C, 62.8; H, 6.1; N, 30.3%; C12H13N5. 1/4 H2O requires: C, 62.2; H, 5.8; N, 30.2 %.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. filtrationThe solid collected by filtration
  4. temperaturewas heated
  5. temperatureat reflux with ethanol
  6. customthe solvent evaporated
  7. washThe residual solid was washed with water
  8. custompurified by flash column chromatography (silica, Merck 9385)
  9. washeluting with ethyl acetate/hexane (1:3)
  10. customThis gave a solid which
  11. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-72ee08255acd45ca9cb6fd0501a10d98
Source dataset
uspto-grants-1994_07
Patent number
US05332737

Reaction notes

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