Methyl iodide → HCID 67974645, Verbindung

HRID 2046197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046197
[H-].[Na+].[OH:3][CH:4]([CH3:24])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[C:8]2[C:7]1=[O:23].I[CH3:26]>C1COCC1>[CH3:26][O:3][CH:4]([CH3:24])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[C:8]2[C:7]1=[O:23]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67974700HCID 67974700, Verbindung

Produkt 1

HCID 67974645HCID 67974645, VerbindungAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 60% dispersion of sodium hydride in mineral oils (8.6 mg, 0.21 mmol) was added to a solution of (rac)-5-(2-hydroxy-propyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (54 mg, 0.18 mmol) in THF (1 mL) at 0° C. The mixture was stirred at 0° C. for 15 minutes and then iodomethane (0.02 mL, 0.36 mmol) was added and the mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction was quenched with a saturated solution of NH4Cl and extracted with AcOEt, dried with (Na2SO4), filtered and the solvent evaporated in vacuo to yield a yellow oil which was purified by flash column chromatography (silica; AcOEt in heptane from 0:100 to 0:100) to yield a colourless oil which was triturated with DIPE to yield (rac)-5-(2-methoxy-propyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (28 mg, 49% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 1.17 (d, J=6.4 Hz, 3H), 3.27 (dd, J=14.0, 7.9 Hz, 1H), 3.33 (s, 3H), 3.60-3.69 (m, 1H), 3.79-3.85 (m, 1H), 3.85-3.90 (m, 1H), 3.93-4.02 (m, 1H), 4.36 (t, J=6.2 Hz, 2H), 5.09 (s, 2H), 6.93 (s, 1H), 6.96 (t, J=7.4 Hz, 1H), 7.00 (d, J=8.1 Hz, 2H), 7.27-7.32 (m, 2H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 hours
  3. customThe reaction was quenched with a saturated solution of NH4Cl
  4. extractionextracted with AcOEt
  5. dry with materialdried with (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto yield a yellow oil which
  9. customwas purified by flash column chromatography (silica; AcOEt in heptane from 0:100 to 0:100)
  10. customto yield a colourless oil which
  11. customwas triturated with DIPE

Quellen und Nachweise

ORD-Eintrag
ord-a612ee4b3e0249c192185648bc1d48cd
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592422B2

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