Ethyl Acetate → (S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholine

HRID 2063361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063361
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4](Cl)[N:3]=1.[CH3:13][C@H:14]1[CH2:19][O:18][CH2:17][CH2:16][NH:15]1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>C(O)C.CN(C=O)C.C(OCC)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][C@@H:14]2[CH3:13])[N:3]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 17125532,6-dichloro-9-methyl-9H-purineHCID 12012220(3S)-3-methylmorpholine

Produkt 1

HCID 58222544(S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholineAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,6-dichloro-9-methyl-9H-purine (1.41 g, 6.96 mmol) and (S)-3-methylmorpholine (817 mg, 8.08 mmol, 1.16 eq.) in anhydrous ethanol (60 mL) and anhydrous DMF (5.0 mL) was added N,N-diisopropylethylamine (1.8 mL, 10.43 mmol, 1.5 eq.), and the reaction mixture was stirred at RT under N2 for 3 days. The reaction mixture was diluted with 1:1 v/v diethyl ether:ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 80% ethyl acetate in hexane) to give the desired compound (a-4) as a solid (1.59 g, 85.2%). 1H NMR (CDCl3, 500 MHz) δ ppm 7.65 (s, 1H), 5.34 (broad d, 2H), 3.99 (m, 1), 3.76 (m, 5H), 3.61 (ddd, 1H), 3.36 (broad s), 1H), 1.39 (d, 3H).

Aufarbeitung

  1. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 80% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e8913a2f6d604bbb84b28d207cf65046
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288381B2

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