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Potassium Carbonate → tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930723
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1930723
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[NH:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.O=[C:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]1[C:33](=O)[CH2:34][CH2:35][CH:36]1[CH2:40][CH2:39][CH2:38][O:37]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:18]=[C:33]([CH2:34][CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][O:37]3)[C:21]3[CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[CH2:24][CH2:25][C:20]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 59333690Tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylateHCID 178493227HCID 178493227, Verbindung

Produkt 1

HCID 59333773tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateAusbeute 28,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A reaction mixture of 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (0.800 g, 2.17 mmol), tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate (0.705 g, 2.17 mmol) and potassium carbonate (0.599 g, 4.33 mmol) in ethanol (6 mL) was stirred at 60° C. overnight. The reaction mixture was transferred to a microwave vial (20 mL) and run in the microwave at 120° C. for 45 minutes. The reaction mixture was filtered and washed with dichloromethane. The filtrate was concentrated and the residue was dissolved in dichloromethane and washed with water, dried (MgSO4) and concentrated. The crude product was purified by silica flash chromatography using a gradient of methanol in dichloromethane (0 to 4%) giving tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.335 g, 28.9%) as the product.

Aufarbeitung

  1. waitrun in the microwave at 120° C. for 45 minutes
  2. filtrationThe reaction mixture was filtered
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by silica flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fdb27e4706544135b8223f8e6aa1c780
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08188101B2

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