Ammonium formate → HCID 23371649, compound

HRID 1899819Notes

Reaction equation

HRID 1899819 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. temperaturewas 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-23f3ce190c02430f8735d6a0ed2f4a1e
Source dataset
uspto-grants-1996_11
Patent number
US05574037

Reaction notes

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