Triethylamine → 10-Chloro-2-(1-methoxypropan-2-yl)-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one

HRID 2234410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234410
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N:9]([CH3:14])[C:10](=[O:13])[CH:11]=[CH2:12])=[CH:4][N:3]=1.[NH2:15][CH:16]([CH3:20])[CH2:17][O:18][CH3:19].C(N(CC)CC)C>[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4].C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]2[C:5]([N:9]([CH3:14])[C:10](=[O:13])[CH2:11][CH2:12][N:15]2[CH:16]([CH3:20])[CH2:17][O:18][CH3:19])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 123458MethoxyisopropylamineHCID 86617580N-(2,4-dichloropyrimidin-5-yl)-N-methyl-prop-2-enamide2×

Produkt 1

HCID 8661754510-Chloro-2-(1-methoxypropan-2-yl)-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-oneAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76524Titanium tetraethoxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(2,4-dichloropyrimidin-5-yl)-N-methyl-prop-2-enamide (Intermediate 113; 318 mg, 1.37 mmol), 2-Amino-1-methoxypropane (152 μl, 1.44 mmol), Triethylamine (382 μl, 2.74 mmol), Titanium Tetra-ethoxide (29 μl, 0.137 mmol) and DCM (5 mL) were combined and stirred at room temperature for 1 hr, heated to 40° C. for 3 hrs, cooled to room temperature, washed with water and gravity filtered through a PTFE. The organic solution was purified by chromatographic separation on silica eluting with a shallow gradient (25 column volumes) of 10-50% Ethyl Acetate/iso-hexane. Product containing fractions were combined and evaporated to give the title compound as a clear gum (54 mg, 18%).

Aufarbeitung

  1. temperatureheated to 40° C. for 3 hrs
  2. temperaturecooled to room temperature
  3. washwashed with water and gravity
  4. filtrationfiltered through a PTFE
  5. customThe organic solution was purified by chromatographic separation on silica eluting with a shallow gradient (25 column volumes) of 10-50% Ethyl Acetate/iso-hexane
  6. additionProduct containing fractions
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3e612f36bfcc4ac7829cf80ae2968019
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709471B2

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