Methanol → HCID 23371638, compound

HRID 1729195Notes

Reaction equation

HRID 1729195 reaction equation
[CH2:1]([CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[N:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([CH3:20])[N:13]=2)[CH2:4]1)[CH3:2].C1(OC2C=CC=CC=2)C=CC=CC=1.CO>[Pd].C(Cl)Cl>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[N:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([CH3:20])[N:13]=2)[CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 7583Diphenyl EtherHCID 23371656HCID 23371656, compound

Product 1

HCID 23371638HCID 23371638, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture 4-(3-ethylindolin-1-yl)-2-methyl-6-methylamino-1,3,5-triazine (1.5 g, 5.6 mM), 30% w/w palladium on charcoal (0.15 g) and diphenyl ether (10 ml) was heated under reflux in an argon atmosphere for 45 minutes. The mixture was cooled to ambient temperature and methanol (10ml) and methylene chloride (20 ml) were added. The catalyst was removed by filtration through diatomaceous earth. The filtrate was evaporated to low volume by distillation in vacuo and then diluted with hexane (50 ml) to give 4-(3-ethylindol-1-yl)-2-methyl-6-methylamino-1,3,5-triazine as a white solid (1.3 g, 87% yield), m.p. 174°-175° C.; microanalysis, found: C,67.3; H,5.9; N,26.2%; C15H17N5 requires C,67.42; H,6.3; N,26.21%.

Workup

  1. temperatureunder reflux in an argon atmosphere for 45 minutes
  2. customThe catalyst was removed by filtration through diatomaceous earth
  3. customThe filtrate was evaporated to low volume by distillation in vacuo
  4. additiondiluted with hexane (50 ml)

Sources & evidence

ORD record
ord-9346d8eca722429f9fc1662577c291f4
Source dataset
uspto-grants-1994_07
Patent number
US05332737

Reaction notes

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