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Potassium Phosphate, Tribasic → 2-chloro-5-((R)-1-(4-chlorophenyl)ethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

HRID 1631724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1631724
Br[C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([NH:17][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH3:19])=[O:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(O)(C)(C)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:5]1[N:6]=[CH:7][C:2]2[N:17]([C@@H:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH3:19])[C:15](=[O:16])[CH:10]3[CH2:11][O:12][CH2:13][CH2:14][N:9]3[C:3]=2[N:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866701084-(5-bromo-2-chloropyrimidin-4-yl)-N-((R)-1-(4-chlorophenyl)ethyl)morpholine-3-carboxamide

Produkt 1

HCID 866701112-chloro-5-((R)-1-(4-chlorophenyl)ethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-oneAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 167845palladium(II) acetateKatalysatorHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To an oven dried vial were added 4-(5-bromo-2-chloropyrimidin-4-yl)-N—((R)-1-(4-chlorophenyl)ethyl)morpholine-3-carboxamide (PREPARATION x31, 574 mg, 1.247 mmol), Xantphos (54.1 mg, 0.094 mmol), potassium phosphate tribasic (265 mg, 1.247 mmol) and palladium(II)acetate (14.00 mg, 0.062 mmol) in dioxane (5 mL) and tert-butanol (1 mL). The reaction mixture was degassed for 5 minutes with N2. The vial was then sealed and heated to 105° C. and the contents were stirred for 72 hours to give a brown suspension. The reaction mixture was subsequently diluted with ethyl acetate and washed with aqueous saturated NH4Cl (3×5 mL) and brine (3×5 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give a crude product which was loaded onto an ISCO® silica gel cartridge (40 g) and eluted using an ethyl acetate/hexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a white solid (58 mg, 12%). 1H NMR (400 MHz, DMSO-d6) δ 1.68-1.80 (m, 3H), 2.91-3.02 (m, 1H), 3.46-3.64 (m, 1H), 3.64-3.76 (m, 1H), 3.88-4.01 (m, 1H), 4.13-4.27 (m, 2H), 4.41-4.60 (m, 1H), 5.99-6.24 (m, 1H), 7.27-7.49 (m, 4H), 7.50-7.57 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C17H16Cl2N4O2, 379.07. found 379.3.

Aufarbeitung

  1. customTo an oven dried vial
  2. customThe reaction mixture was degassed for 5 minutes with N2
  3. customThe vial was then sealed
  4. customto give a brown suspension
  5. washwashed with aqueous saturated NH4Cl (3×5 mL) and brine (3×5 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a crude product which
  10. washeluted
  11. customThe product was collected
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b929ca664384459991ca54a1216acd8
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08791107B2

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