Acetaldehyde → 1-[6-ethylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1428880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428880
[CH:1](=O)[CH3:2].[CH2:4]([O:6][C:7]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22](=[O:32])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH2:33])[CH:20]=3)[N:15]=2)[CH:13]=1)=[O:8])[CH3:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C.CCOC(C)=O>[CH2:4]([O:6][C:7]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22](=[O:32])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:33][CH2:1][CH3:2])[CH:20]=3)[N:15]=2)[CH:13]=1)=[O:8])[CH3:5]

Komponenten

6

Edukt 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 684879131-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 684855101-[6-ethylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl esterAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Acetaldehyde (1 mL) was added to 1-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.250 g, 0.582 mol) and 4 Å molecular sieves (0.35 g) in ethanol (1.9 g). The reaction mixture was stirred at room temperature for 18 h and was then filtered. Ethanol and acetaldehyde were removed under high vacuum. The residue was redissolved in DCE (1.5 mL) and sodium triacetoxyborohydride (0.308 g, 1.46 mmol) was added. The reaction mixture was stirred at room temperature for 6 d, then diluted with EtOAc (30 mL) and washed with saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was extracted with EtOAc (30 mL) and the combined organic layers were washed with brine (20 mL), dried (MgSO4), and concentrated. The residue was purified via FCC (5-65% EtOAc/hexanes) to yield the titled compound (87.0 mg, 33% yield). MS (ESI/Cl): mass calcd. for C22H31N5O4Si, 457.2; m/z found, 458.2 [M+H]+.

Aufarbeitung

  1. filtrationwas then filtered
  2. customEthanol and acetaldehyde were removed under high vacuum
  3. dissolutionThe residue was redissolved in DCE (1.5 mL)
  4. stirringThe reaction mixture was stirred at room temperature for 6 d
  5. washwashed with saturated aqueous sodium bicarbonate (20 mL)
  6. extractionThe aqueous layer was extracted with EtOAc (30 mL)
  7. washthe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified via FCC (5-65% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-13a8f5857df54754b9b2807d5a1a8379
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937078B2

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