2-(Trifluoromethyl)aniline → 4-N-[2-(trifluoromethyl)phenyl]pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 2287705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2287705
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](SC)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.Cl.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:25])([F:24])[F:23].NC1C=CC=CC=1C(F)(F)F.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:23])([F:24])[F:25])=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 69222-(Trifluoromethyl)anilineHCID 516892Sodium BicarbonateHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidineHCID 22736790Alpha,alpha,alpha-trifluoro-O-toluidine hydrochloride

Produkt 1

HCID 53280574-N-[2-(trifluoromethyl)phenyl]pyrido[4,3-d]pyrimidine-4,7-diamineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584188Chloroform methanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (300 mg, 1.56 mmol), 2-aminobenzotrifluoride hydrochloride (1.00 g, 5.06 mmol) and 2-aminobenzotrifluoride (2.00 g, 12.4 mmol) is stirred at 160° C. for 10 min. The resulting product is neutralized with excess NaHCO3, dissolved in MeOH/CHCl3, dried onto silica gel and chromatographed over silica gel (6-7% MeOH/CH2Cl2) to give 7-amino-4-(2-trifluoromethylanilino)pyrido[4,3-d]pyrimidine (194 mg, 41%) as a cream solid, mp (MeOH/CHCl3 /light petroleum) 126-130° C. (dec.). 1H NMR (DMSO) δ 10.60 (1H, brs), 9.17 (1H, brs), 8.13 (1H, brs), 7.76, 7.69 (1H, 1H, m, m), 7.45 (2H, m), 6.66 (2H, brs), 6.36 (1H, s).

Aufarbeitung

  1. customdried onto silica gel
  2. customchromatographed over silica gel (6-7% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-9fb8c8cb8f79493599435b58936c2691
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06084095

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