Potassium Carbonate → HCID 178463038, Verbindung

HRID 630173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630173
[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:22]([CH2:23][CH3:24])[N:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:23]([N:22]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:19][CH:20]=[N:21]1)[CH3:24]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 59589331HCID 59589331, VerbindungHCID 178429541HCID 178429541, Verbindung

Produkt 1

HCID 178463038HCID 178463038, VerbindungAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

6-methyl-2-sulfanylpyrimidin-4-ol (927 mg, 6.5 mmol) was dissolved in anhydrous DMF (30 mL), then potassium carbonate (2.70 g, 19.6 mmol) and 5-(bromomethyl)-1-ethyl-1H-pyrazole (8.5 mmol) in DMF (10 mL) were added. The mixture was stirred overnight 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/MeOH to afford 2-{[(1-ethyl-1H-pyrazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (265 mg, 16% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.32 (t, J=7.0 Hz, 3H), 2.21 (s, 3H), 4.15 (q, J=7.2 Hz, 2H), 4.50 (s, 2H), 6.04 (bs, 1H), 6.22 (d, J=1.7 Hz, 1H), 7.33 (d, J=1.7 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/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-1095e48bc049440481877d8e77b89b0c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315521B2

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