1,1,3,3-Tetramethylguanidine → Ethyl 2-acetoxy-2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate

HRID 2047076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047076
[C:1]([O:4][CH:5](P(OCC)(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[Li+].[Cl-].CN(C)C(N(C)C)=N.[CH3:29][Si:30]([CH3:61])([CH3:60])[CH2:31][CH2:32][O:33][CH2:34][N:35]([CH2:52][O:53][CH2:54][CH2:55][Si:56]([CH3:59])([CH3:58])[CH3:57])[C:36]1[N:41]2[N:42]=[CH:43][CH:44]=[C:40]2[N:39]=[C:38]([CH:45]2[CH2:50][CH2:49][C:48](=O)[CH2:47][CH2:46]2)[CH:37]=1>C1COCC1.C(Cl)Cl>[C:1]([O:4][C:5](=[C:48]1[CH2:49][CH2:50][CH:45]([C:38]2[CH:37]=[C:36]([N:35]([CH2:52][O:53][CH2:54][CH2:55][Si:56]([CH3:59])([CH3:58])[CH3:57])[CH2:34][O:33][CH2:32][CH2:31][Si:30]([CH3:61])([CH3:29])[CH3:60])[N:41]3[N:42]=[CH:43][CH:44]=[C:40]3[N:39]=2)[CH2:46][CH2:47]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 664601,1,3,3-TetramethylguanidineHCID 433294Lithium ChlorideHCID 4131038Ethyl 2-(acetyloxy)-2-(diethyl phosphono)acetateHCID 66583636HCID 66583636, Verbindung

Produkt 1

HCID 67494543Ethyl 2-acetoxy-2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a 100 mL roundbottom flask was charged ethyl 2-acetoxy-2-(diethoxyphosphoryl)acetate (1121 mmol, 3.16 g), LiCl (11.21 mmol, 475 mg), and THF (25 mL). The flask was then flushed with argon, sealed, and cooled to −78° C. in a dry ice/IPA bath. Added dropwise to this solution was a solution of 1,1,3,3-tetramethylguanidine (11.21 mmol. 1.41 g) in THF (5 mL). The resulting solution was allowed to stir at −78° C. for 30 minutes. At 30 minutes, 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone (5.09 mmol, 2.50 g) was added in THF (3 mL). The reaction was then allowed to slowly warm to room temperature and then stirred for 48 hours. After 48 hours, the reaction was diluted with DCM (100 mL) and washed with H2O (50 mL). The organic layer was collected, dried over Na2SO4, and reduced in vacuo. The resulting residue was purified via flash chromatography to yield the title compound.

Aufarbeitung

  1. customThe flask was then flushed with argon
  2. customsealed
  3. additionAdded dropwise to this solution
  4. waitAt 30 minutes
  5. temperatureto slowly warm to room temperature
  6. stirringstirred for 48 hours
  7. waitAfter 48 hours
  8. washwashed with H2O (50 mL)
  9. customThe organic layer was collected
  10. dry with materialdried over Na2SO4
  11. customThe resulting residue was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-645dd3294d7c41909f29b44c35b47f7c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591943B2

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