Benzylamine → 2-Methylthio-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

HRID 1290663

Reaktionsgleichung

Reaktionsgleichung von HRID 1290663
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:10]=1[O:11][C:12]1[N:17]=[C:16]([S:18][CH3:19])[N:15]=[C:14](Cl)[C:13]=1[N+:21]([O-:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:10]=1[O:11][C:12]1[N:17]=[C:16]([S:18][CH3:19])[N:15]=[C:14]([NH:43][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:13]=1[N+:21]([O-:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 221029862-Methylthio-4-chloro-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

Produkt 1

HCID 189168492-Methylthio-4-benzylamino-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 6-(2-benzyloxy-5-cyanophenoxy)-4-chloro-5-nitro-2-methylthiopyrimidine (2.5 g, 5.83 mmol) in 50 mL acetonitrile at 0° C. was added cesium carbonate (2.47 g, 7.58 mmol) followed by benzylamine (0.64 mL) and the reaction mixture was heated at 50° C. for 4 hours. The reaction was filtered, the filtrate evaporated and the residue chromatographed on silica gel (ethyl acetate:hexane) to afford 1.82 g (65%) of 6-(2-benzyloxy-5-cyanophenoxy)-4-(benzyl)amino-5-nitro-2-methylthiopyrimidine, a compound of formula (E).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated
  3. customthe residue chromatographed on silica gel (ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4eca00698592454faa2b92ea65d77acf
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753635

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