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Sodium Carbonate → 2-(2,6-dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methyl-6-[(3R)-3-methylpiperazin-1-yl]pyrimidine

HRID 1091956
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1091956
Cl[C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=2[CH3:19])=[C:6]([CH3:20])[N:5]=[C:4]([C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:28])[N:3]=1.[CH3:29][C@@H:30]1[CH2:35][NH:34][CH2:33][CH2:32][NH:31]1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:21]=1[C:4]1[N:5]=[C:6]([CH3:20])[C:7]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=2[CH3:19])=[C:2]([N:34]2[CH2:33][CH2:32][NH:31][C@H:30]([CH3:29])[CH2:35]2)[N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 73304342-Methylpiperazine, (R)-HCID 575314014-Chloro-2-(2,6-dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidine

Produkt 1

HCID 575314072-(2,6-dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methyl-6-[(3R)-3-methylpiperazin-1-yl]pyrimidine

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-2-(2,6-dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidine (0.1 mmol in 0.5 mL DMA), (R)-2-methyl-piperazine (40 mg) and sodium carbonate (85 mg) is heated at 100° C. with agitation for 18 h. The reaction mixture is allowed to cool and partitioned between EtOAc (6 mL) and water (2 mL). The organic layer is separated, washed with water (2 mL×2), brine (2 mL), dried over anhydrous sodium sulfate, filtered and evaporated to obtain a colorless oil. Purification by chromatography on silica gel (2% MeOH/DCM/0.1% Ammonium hydroxide) provides the title compound as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.06-7.26 (m, 4H), 6.79-6.82 (m, 2H), 4.97 (dd, 2H), 3.89-3.96 (m, 2H), 2.87-3.05 (m, 5H), 2.62-2.69 (m, 1H), 2.56 (s, 3H), 2.23 (s, 3H), 2.16 (s, 6H), 1.27 (d, J=6.8 Hz, 6H), 0.93 (d, J=6.6 Hz, 3H).

Aufarbeitung

  1. temperatureto cool
  2. custompartitioned between EtOAc (6 mL) and water (2 mL)
  3. customThe organic layer is separated
  4. washwashed with water (2 mL×2), brine (2 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a colorless oil
  9. customPurification by chromatography on silica gel (2% MeOH/DCM/0.1% Ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-ac8a46050d424f4e9f2e7e37cd822d5a
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129395B2

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