Potassium Carbonate → HCID 178429526, Verbindung

HRID 630113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630113
Cl.[Cl:2][C:3]1[N:7]([CH3:8])[CH:6]=[N:5][C:4]=1[CH2:9]Cl.[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:2][C:3]1[N:7]([CH3:8])[CH:6]=[N:5][C:4]=1[CH2:9][S:18][C:16]1[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 668208135-chloro-4-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 178429541HCID 178429541, Verbindung

Produkt 1

HCID 178429526HCID 178429526, VerbindungAusbeute 246,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 5-chloro-4-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (463 mg, 2.3 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (213 mg, 1.5 mmol), and potassium carbonate (1.1 g, 8.0 mmol) in acetone (15 mL) was stirred at room temperature overnight. The solid material was removed by filtration and washed with 50% acetone/MeOH (2×15 mL). The filtrate was recovered and evaporated. The crude product was purified by flash chromatography (0-10% MeOH/DCM and 0-6% MeOH/DCM), affording 2-{[(5-chloro-1-methyl-1H-imidazol-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (1.0 g, 93% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.17 (s, 3H), 3.53 (s, 3H), 4.25 (s, 2H), 5.97 (s, 1H), 7.70 (s, 1H); M+271. The product was used without further purification.

Aufarbeitung

  1. customThe solid material was removed by filtration
  2. washwashed with 50% acetone/MeOH (2×15 mL)
  3. customThe filtrate was recovered
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (0-10% MeOH/DCM and 0-6% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a72ee647e55a458db2434f13407e5371
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315521B2

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