2,4,6-Trimethylaniline → 2,5,6-trichloro-N-(2,4,6-trimethylphenyl)4-pyrimidinamine

HRID 41365

Reaktionsgleichung

Reaktionsgleichung von HRID 41365
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.[CH3:11][C:12]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:13]=1[NH2:14].CC(N(C(C)C)CC)C>O1CCOCC1>[Cl:10][C:4]1[C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=[C:2]([NH:14][C:13]2[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:12]=2[CH3:11])[N:3]=1.[Cl:1][C:2]1[N:3]=[C:4]([NH:14][C:13]2[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:12]=2[CH3:11])[C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=1

Komponenten

6

Edukt 3

HCID 69132,4,6-TrimethylanilineHCID 156902,4,5,6-TetrachloropyrimidineHCID 81531Diisopropylethylamine

Produkt 2

HCID 221700912,5,6-trichloro-N-(2,4,6-trimethylphenyl)4-pyrimidinamineHCID 221700944,5,6-trichloro-N-(2,4,6-trimethylphenyl)-2-pyrimidinamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

2,4,5,6-tetrachloropyrimidine (0.0134 mol), 1,4-dioxane (30 ml), 2,4,6-trimethyl aniline (0.0134 mol), and N,N-bis(1-methylethyl)ethanamine (0.0136 mol) were added to a flask under argon and stirred at 55° C. for 16 hours. The solvent was evaporated, and the residue was dissolved in CH2Cl2, then purified by column chromatography over silica gel (eluent: CH2Cl2/hexane ¼, and ½). The desired fractions were collected and their solvent was evaporated, yielding 0.15 g 4,5,6-trichloro-N-(2,4,6-trimethylphenyl)-2-pyrimidinamine (interm. 6) and 3.15 g 2,5,6-trichloro-N-(2,4,6-trimethylphenyl)-4-pyrimidinamine (interm. 7).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. custompurified by column chromatography over silica gel (eluent: CH2Cl2/hexane ¼, and ½)
  4. customThe desired fractions were collected
  5. customtheir solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-489dd9ecf56a4150bd590657d4a5ef5d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530655B2

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