Sodium Hydroxide → HCID 178432946, Verbindung

HRID 1840636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840636
[CH3:1][C:2]1([NH2:8])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:10]1[N:11](C(=O)C)[CH2:12][C:13]2[N:19]=[C:18]([Cl:20])[N:17]=[C:16]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=3)[C:14]=2[N:15]=1.[OH-].[Na+]>CO>[NH2:8][C:2]1([CH3:1])[CH2:7][CH2:6][N:5]([C:10]2[NH:11][CH2:12][C:13]3[N:19]=[C:18]([Cl:20])[N:17]=[C:16]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=4)[C:14]=3[N:15]=2)[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 210904454-Methylpiperidin-4-amineHCID 225929701-[2,6-Dichloro-8-(3-chloro-4-fluorophenylamino)-4H-pyrimido[5,4-d]pyrimidin-3-yl]ethanone

Produkt 1

HCID 178432946HCID 178432946, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

At 60° C. a mixture of 30.8 g (0.270 mol) of 4-methylpiperidin-4-ylamine and 100 ml of methanol is added dropwise to a suspension of 100 g (0.257 mol) of (3) in 690 ml of methanol. The mixture is stirred for 1 hour at 60° C., allowed to cool to 40° C., 280 ml of 2N sodium hydroxide solution are added and the resulting mixture is stirred for 3 hours at 60° C. Then 300 ml of methanol are distilled off and 600 ml of water are added. The mixture is stirred for 5 minutes at ambient temperature, filtered off and the residue is washed with 250 ml of water, 3 times 50 ml of acetone and 100 ml of methyl-tert-butylether and dried at 40° C. in vacuo. Yield: 100.5 g (92.2%), melting point 211.5° C. 400 MHz-1H-NMR (DMSO) (ppm)=8.55 br s, 1H, NH; 8.05 dd, 1H, aniline-H; 7.78 ddd, 1H, aniline-H; 7.47 t, 1H, aniline-H; 6.90 br s, 1H, NH; 4.28 s, 2H, CH2; 3.68 m, 2H, CH2; 3.45 m, 2H, CH2, 3.32 br s, 2H, NH2; 1.37 m, 4H, 2CH2; 1.05 s, 3H, CH3.

Aufarbeitung

  1. temperatureto cool to 40° C.
  2. stirringthe resulting mixture is stirred for 3 hours at 60° C
  3. distillationThen 300 ml of methanol are distilled off
  4. addition600 ml of water are added
  5. stirringThe mixture is stirred for 5 minutes at ambient temperature
  6. filtrationfiltered off
  7. washthe residue is washed with 250 ml of water, 3 times 50 ml of acetone and 100 ml of methyl-tert-butylether
  8. customdried at 40° C. in vacuo
  9. custom4.28 s, 2H, CH2
  10. custom1.05 s, 3H, CH3

Quellen und Nachweise

ORD-Eintrag
ord-f63a55facde64bb2b374a8590f9b33c6
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680384B2

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