Diethyl Ether → 2-Butyl-3,5,7,8-tetrahydro-4-oxo-pyrido[4,3-d]pyrimidine-6(4H)-carboxylic acid 2-(trimethylsilyl)ethyl ester

HRID 487536

Reaktionsgleichung

Reaktionsgleichung von HRID 487536
[CH3:1][Si:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([C:15]([O:17]CC)=O)[CH2:9]1)=[O:7].Cl.[C:23]([NH2:29])(=[NH:28])[CH2:24][CH2:25][CH2:26][CH3:27].C[O-].[Na+].CCOCC>C(O)C.CO.O>[CH3:21][Si:2]([CH3:1])([CH3:20])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:28]=[C:23]([CH2:24][CH2:25][CH2:26][CH3:27])[NH:29][C:15](=[O:17])[C:10]=2[CH2:9]1)=[O:7]

Komponenten

8

Edukt 4

HCID 3283Diethyl EtherHCID 10942334Sodium MethoxideHCID 11615174Pentanimidamide HydrochlorideHCID 545371754-Oxo-1,3-piperidinedicarboxylic acid 3-ethyl 1-[2-(trimethylsilyl)ethyl]ester

Produkt 1

HCID 1363783822-Butyl-3,5,7,8-tetrahydro-4-oxo-pyrido[4,3-d]pyrimidine-6(4H)-carboxylic acid 2-(trimethylsilyl)ethyl esterAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 2.2 g of 4-oxo-1,3-piperidinedicarboxylic acid 3-ethyl 1-[2-(trimethylsilyl)ethyl]ester and 1.2 g of valeramidine hydrochloride in 15 ml of dry ethyl alcohol is added 7 ml of 1M sodium methoxide in methanol. The resulting mixture is stirred and heated under reflux for 25 minutes. The reaction mixture is allowed to cool, filtered and the solid washed with ethyl alcohol. The combined filtrates are evaporated in vacuo without heat to give an oily solid. Ether and water are added to the residue followed by refrigeration. The resulting crystalline solid is collected, washed with ether and air dried to give 0.8 g of the desired product as a crystalline solid, m.p. 152°-155° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 25 minutes
  3. temperatureto cool
  4. filtrationfiltered
  5. washthe solid washed with ethyl alcohol
  6. customThe combined filtrates are evaporated in vacuo
  7. temperaturewithout heat
  8. customto give an oily solid
  9. customThe resulting crystalline solid is collected
  10. washwashed with ether and air
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9f3e222c635f4699b0f8cc55846eb83b
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296480

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