Potassium Carbonate → HCID 178429487, Verbindung

HRID 577040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577040
[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]=[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]2[CH:26]=1>CN(C=O)C>[N:19]1[C:18]([CH2:17][S:8][C:6]2[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:26][N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=12

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 4318932-(bromomethyl)imidazo[1,2-a]pyridineHCID 178429541HCID 178429541, Verbindung

Produkt 1

HCID 178429487HCID 178429487, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-methyl-2-sulfanylpyrimidin-4-ol (638 mg, 4.5 mmol) was dissolved in anhydrous DMF (20 mL), then potassium carbonate (1.86 g, 13.5 mmol) and 2-(bromomethyl)imidazo[1,2-a]pyridine (1.42 g, 6.7 mmol) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with methanol, where the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 12% DCM/MeOH to afford 2-({imidazo[1,2-a]pyridin-2-ylmethyl}sulfanyl)-6-methylpyrimidin-4-ol as a white solid (631 mg, 52% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.46 (s, 2H), 5.99 (bs, 1H), 6.84 (dt, J=1.7 Hz, J=6.7 Hz, 1H), 7.17-7.22 (m, 1H), 7.45 (dd, J=9.0 Hz, J=0.8 Hz, 1H), 7.86 (s, 1H), 8.46-8.49 (m, 1H); LRMS (ES+) m/z 273 (60%, M+1).

Aufarbeitung

  1. customThe solid was removed by filtration
  2. washwashed with methanol, where the filtrate
  3. customwas evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 12% DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-ac4482cb18764aa8ae82d6cbc840fbc3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

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