Dichloromethane → HCID 178433069, Verbindung

HRID 1371109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371109
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:24][N:25]([CH3:27])[CH3:26].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O>[CH3:26][N:25]([CH3:27])[CH2:24][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][N:18]1[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2[C:3]=1[N:11]=[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]=2

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 252484N-(2-Piperidylmethyl)-dimethylamineHCID 178432852HCID 178432852, Verbindung

Produkt 1

HCID 178433069HCID 178433069, VerbindungAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (88.3 mg, 0.36 mmol) and N-(2-piperidylmethyl)-dimethylamine (Salor Chemical Company) (0.25 g, 1.72 mmol) was added a solution of K2CO3 (0.25 g, 1.60 mmol) in H2O (2.5 mL). This mixture was stirred at 140° C. in a closed-capped Wheaton vial for 2.5 h. After cooling, CH2Cl2 (10 mL) and H2O (10 mL) were added. The organic solution was removed and the aqueous solution was washed with CH2Cl2 (10 mL). The combined organic solutions were washed with saturated NaCl (15 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel) to give 43 mg (34%) of the title compound as a yellow oil. MS m/z: 350 (M+1), 305, 214. 1H NMR (DMSO-d6; 400 MHz): δ 1.63 (m, 6), 2.29 (s, 6), 2.40 (s, 3), 2.81 (m, 2), 3.03 (br t, 1, J=11.8), 4.53-4.63 (m, 2), 6.75 (s, 1), 7.37 (m, 1), 7.50 (t, 2, J=7.5), 7.81 (d, 2, J=7.8), 12.47 (s, 1).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe organic solution was removed
  3. washthe aqueous solution was washed with CH2Cl2 (10 mL)
  4. washThe combined organic solutions were washed with saturated NaCl (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-2a5f7bfa495244e3bf1b8a7b4069c183
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583154B1

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