Potassium Carbonate → HCID 178429515, Verbindung

HRID 577047

Reaktionsgleichung

Reaktionsgleichung von HRID 577047
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[N:19]=[CH:20][S:21][CH:22]=1>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:17][C:18]2[N:19]=[CH:20][S:21][CH:22]=2)[N:5]=[C:4]([OH:9])[CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 98989844-(Bromomethyl)thiazoleHCID 178429541HCID 178429541, Verbindung

Produkt 1

HCID 178429515HCID 178429515, VerbindungAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-methyl-2-sulfanylpyrimidin-4-ol (491 mg, 3.4 mmol) was dissolved in anhydrous DMF (25 mL), then potassium carbonate (1.43 g, 10.3 mmol) and 4-(bromomethyl)-1,3-thiazole (922 mg, 5.2 mmol) were added. The mixture was stirred for 4 hours at room temperature. The solid was removed by filtration and washed with methanol, and the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 10% DCM in MeOH to afford to 6-methyl-2-[(1,3-thiazol-4-ylmethyl)sulfanyl]pyrimidin-4-ol (268 mg, 32% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.53 (s, 2H), 6.00 (bs, 1H), 7.63 (d, J=2.0 Hz, 1H), 9.06 (d, J=2.0 Hz, 1H).

Aufarbeitung

  1. customThe solid was removed by filtration
  2. washwashed with methanol
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 10% DCM in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-23742779b6794157b034c7fab04a73ef
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

Verknüpfte Notizen

Wird geladen…