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Dimethylformamide → 2-Chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine

HRID 1850484
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1850484
CN(C=O)C.[CH3:6][C:7]1([CH3:25])[CH2:11][C:10]2[C:12]([CH3:24])=[C:13]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1.[Cl:26][C:27]1[N:32]=[C:31]([Cl:33])[CH:30]=[CH:29][N:28]=1.C(N(CC)CC)C>O>[Cl:26][C:27]1[N:32]=[C:31]([N:21]2[CH2:20][CH2:19][N:18]([C:13]3[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]4[O:8][C:7]([CH3:25])([CH3:6])[CH2:11][C:10]=4[C:12]=3[CH3:24])[CH2:23][CH2:22]2)[CH:30]=[CH:29][N:28]=1.[Cl:33][C:31]1[CH:30]=[CH:29][N:28]=[C:27]([N:21]2[CH2:20][CH2:19][N:18]([C:13]3[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]4[O:8][C:7]([CH3:25])([CH3:6])[CH2:11][C:10]=4[C:12]=3[CH3:24])[CH2:23][CH2:22]2)[N:32]=1
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Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 667597311-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

Produkt 2

HCID 594850032-Chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidineAusbeute 62 %
HCID 59485115
4-Chloro-2-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine
Ausbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To the DMF (10 mL) solution of 1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (1.92 g, 7.00 mmol) synthesized in Reference example 61, 2,4-dichloropyrimidine (1.04 g, 7.00 mmol) and triethylamine (1.07 mL, 7.70 mmol) were added and the mixture was stirred at room temperature for 1 hour. To the mixture solution, water was added. The extraction was carried out by using ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5-85:15) to obtain 2-chloro-4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine 1.68 g (ethyl acetate/hexane=4:1, Rf=0.1, yield 62%) and 4-chloro-2-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]pyrimidine 100 mg (ethyl acetate/hexane=4:1, Rf=0.5, yield 4%).

Aufarbeitung

  1. additionwere added
  2. extractionThe extraction
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. customThen, the solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5-85:15)

Quellen und Nachweise

ORD-Eintrag
ord-9442a5ed28bd4b2580e95d4722857b1b
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957069B2

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