Tetrahydrofuran → 2-{2-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-propan-2-ol

HRID 1855467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855467
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22](OCC)=O)[CH:19]=[C:18](C)[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.C[Mg]Cl.[C:31](=O)([O-])[O-].[Na+].[Na+].[O:37]1[CH2:41][CH2:40]CC1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:17]=[C:18]([C:41]([OH:37])([CH3:40])[CH3:31])[CH:19]=[C:20]([CH3:22])[N:21]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 10340Sodium CarbonateHCID 57829752HCID 57829752, VerbindungHCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 441922492-{2-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidin-4-yl}-propan-2-ol

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6-methyl-pyrimidine-4-carboxylate (184 mg, 0.5 mmol) in tetrahydrofurane (10 mL) was added at 0° C. over 2 min a 3 M solution of methylmagnesiumchloride in tetrahydrofurane (0.55 mL, 1.65 mmol). The reaction mixture was stirred at 0° C. for 15 min followed by 1 h at 20° C. The mixture was poured on saturated sodium carbonate solution (20 mL) and the product was extracted with ethyl acetate (40 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate and evaporated under reduced pressure. The residual material was crystallized from dichloromethane/heptane to give the title compound to give the title compound (105 mg, 59%) as an off-white solid. MS ISP (m/e): 354.3 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.76 (d, 1H), 7.63 (s, 1H), 7.18 (d, 1H), 7.02 (dd, 1H), 6.88 (s, 1H), 6.75 (s, 1H), 4.04 (s, 1H), 3.88 (s, 3H), 2.47 (s, 3H), 2.30 (s, 3H), 1.53 (s, 6H).

Aufarbeitung

  1. waitfollowed by 1 h at 20° C
  2. extractionthe product was extracted with ethyl acetate (40 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residual material was crystallized from dichloromethane/heptane

Quellen und Nachweise

ORD-Eintrag
ord-71292290cc284aa186d92ac0ca4734bc
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962834B2

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