Sodium ethoxide → tert-Butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930710
[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][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[O-]CC.[Na+]>C(O)C>[CH2:34]([C:33]1[C:21]2[CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25][C:20]=2[N:17]=[C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:18]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 59333761Tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylateHCID 178493227HCID 178493227, Verbindung

Produkt 1

HCID 59333725tert-Butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (300 mg, 1.22 mmol, example 43a), tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylate (466 mg, 1.47 mmol, example 41d) and sodium ethoxide (83 mg, 1.22 mmol) in ethanol (4 mL) were heated at 100° C. in a microwave reactor for 20 minutes. The reaction mixture was allowed to reach room temperature and the solvent was evaporated under reduced pressure. The crude was dissolved in ethyl acetate and washed with water. The organic phase was dried under MgSO4 and the solvent was evaporated under reduced pressure yielding tert-butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (590 mg, 92%) which was used in the subsequent step as such. MS (ES+) m/z 527.3 (M+H)+

Aufarbeitung

  1. customto reach room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe crude was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe organic phase was dried under MgSO4
  6. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0a5a5da9c18b466ba64f8af44c1415ad
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188101B2

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