Stannous chloride dihydrate → HCID 18516946, Verbindung

HRID 1370093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1370093
[C:1]([C:3]1[C:4]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)=[N:7][CH:8]=1)#[N:2].O.O.[Sn](Cl)Cl>C(O)C>[NH2:16][C:12]1[CH:11]=[C:10]([NH:9][C:6]2[N:5]=[C:4]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[C:3]([C:1]#[N:2])=[CH:8][N:7]=2)[CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 18516888HCID 18516888, Verbindung

Produkt 1

HCID 18516946HCID 18516946, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-3-Aminophenyl-5-cyano-4-thien-2-ylpyrimidine-2-amine was prepared by heating a solution of 5-cyano-N-3-nitrophenyl-4-thien-2-ylpyrimidine-2-amine (2.77 g, 8.57 mmol) and tin(II)chloride dihydrate (7.73 g, 34.05 mmol) in ethanol (160 mL) at reflux for 18 h. On cooling the reaction was concentrated under reduced pressure and partitioned between CH2Cl2 and 2M NaOH. The organic phase was dried (MgSO4) and evaporated to give the desired material (320 mg) as a yellow solid, m.p. 221-222°. δH (d6 DMSO) 10.16 (1H, s), 8.83 (1H, s), 8.24 (1H, d, J 3.9 Hz), 7.97 (1H, d, J 5.1 Hz), 7.32 (1H, dd, J 5.0, 4.0 Hz), 6.97 (3H, bm), 6.31 (1H, m) and 5.04 (2H, bs).

Aufarbeitung

  1. temperatureat reflux for 18 h
  2. temperatureOn cooling the reaction
  3. concentrationwas concentrated under reduced pressure
  4. custompartitioned between CH2Cl2 and 2M NaOH
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f4a2f86685fa459a8ba83ed881e0b6f1
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579983B1

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