3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → Tert-butyl 3-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)azetidine-1-carboxylate

HRID 2091850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091850
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[C:10]([CH2:12]P(=O)(OC)OC)[CH:9]=[CH:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].O=[C:34]1[CH2:37][N:36]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:35]1>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:5]2[N:11]=[C:10]([CH:12]=[C:34]3[CH2:35][N:36]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:37]3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 2724682Lithium diisopropylamideHCID 58405032Dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate

Produkt 1

HCID 58404986Tert-butyl 3-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)azetidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a suspension of dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate (0.32 g) in anhydrous THF (3 mL) at 0° C. was added 2.0 M of lithium diisopropylamide in tetrahydrofuran (1.4 eq). The resulting solution was allowed to warm to RT (room temperature) before adding a solution of tert-butyl 3-oxoazetidine-1-carboxylate (1.4 eq) in anhydrous THF (3 mL). The reaction mixture was stirred at room temperature for 1 h, then partitioned between brine and DCM. The organic layer was isolated, dried (MgSO4) and concentrated in vacuo to give 0.34 g of crude tert-butyl 3-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)azetidine-1-carboxylate.

Aufarbeitung

  1. custompartitioned between brine and DCM
  2. customThe organic layer was isolated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bd9371e0e2b94f848af21d18982f6140
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440651B2

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