Diisopropylethylamine → Tert-butyl 2-(2-((1-(cyclohexylmethyl)piperidine-4-yl)(methyl)amino)-2-oxoethoxy)-4,6-dimethylpyrimidine-5-ylcarbamate

HRID 2046326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046326
Br[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.[CH3:18][C:19]1[C:24]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:23]([CH3:33])[N:22]=[C:21]([O:34][CH2:35][C:36]([N:38]([CH3:45])[CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[O:37])[N:20]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:3]1([CH2:2][N:42]2[CH2:41][CH2:40][CH:39]([N:38]([CH3:45])[C:36](=[O:37])[CH2:35][O:34][C:21]3[N:20]=[C:19]([CH3:18])[C:24]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[C:23]([CH3:33])[N:22]=3)[CH2:44][CH2:43]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 137636Cyclohexane, (bromomethyl)-HCID 516892Sodium BicarbonateHCID 59336171Tert-butyl 4,6-dimethyl-2-(2-(methyl(piperidine-4-yl)amino)-2-oxoethoxy)pyrimidine-5-ylcarbamate

Produkt 1

HCID 59336176Tert-butyl 2-(2-((1-(cyclohexylmethyl)piperidine-4-yl)(methyl)amino)-2-oxoethoxy)-4,6-dimethylpyrimidine-5-ylcarbamateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Bromomethyl cyclohexane (25 μL) and diisopropylethylamine (63 μL) were added to a solution of Compound 31 (71 mg) in dimethylformamide (1 mL) and the mixture was stirred at 120° C. for 8 hours. Subsequently, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.; NH-DM1020) column chromatography (hexane:ethyl acetate=1:1) to give 40 mg (46% yield) of the desired product.

Aufarbeitung

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.; NH-DM1020) column chromatography (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-fc51472f410e42e69ff36b929aaf972f
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592435B2

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