HCID 19754149, compound → HCID 19754245, compound

HRID 1588482Notes

Reaction equation

HRID 1588482 reaction equation
[N:1]1([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][CH3:18])[N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>[Pd].C1(OC2C=CC=CC=2)C=CC=CC=1>[N:1]1([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][CH3:18])[N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 19754149HCID 19754149, compound

Product 1

HCID 19754245HCID 19754245, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7583Diphenyl EtherSolvent

Procedure

A mixture of 4-(1-indolinyl)-6-methyl-2-methylaminopyrimidine (2.4 g, 0.01M), 30% w/w palladium on charcoal (0.24 g) and diphenyl ether (10 ml) was heated under reflux in an argon atmosphere for 1 hour. The catalyst was then removed by filtration. The filtrate was then diluted with a large volume of hexane (100 ml). This gave a pale yellow solid which was recrystallised from 2-propanol to give 4-(1-indolyl)-6-methyl-2-methylaminopyrimidine (1.47 g, 62%), m.p. 160°-162° C.; microanalysis, found: C,70.5; H,5.9; N,23.6%; C14H14N4 requires C,70.6; H,5.9; N,23.5%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in an argon atmosphere for 1 hour
  3. customThe catalyst was then removed by filtration
  4. additionThe filtrate was then diluted with a large volume of hexane (100 ml)
  5. customThis gave a pale yellow solid which
  6. customwas recrystallised from 2-propanol

Sources & evidence

ORD record
ord-bf400c72632b4832a737565f2ec1b568
Source dataset
uspto-grants-1993_06
Patent number
US05223505

Reaction notes

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