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Cesium carbonate → (R)-tert-butyl 3-((5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

HRID 1507494
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1507494
I[C:2]1[C:3]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[N:4][C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:6][C:7]=1[O:8][CH3:9].[N:30]1([C:35]2[S:36][CH:37]=[C:38](B3OC(C)(C)C(C)(C)O3)[N:39]=2)[CH:34]=[CH:33][CH:32]=[CH:31]1.C([O-])([O-])=O.[Cs+].[Cs+]>[Pd+2].Cl[Cu].CN(C=O)C>[N:30]1([C:35]2[S:36][CH:37]=[C:38]([C:2]3[C:3]([NH:16][C@@H:17]4[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:18]4)=[N:4][C:5]([N:10]4[CH2:11][CH2:12][O:13][CH2:14][CH2:15]4)=[N:6][C:7]=3[O:8][CH3:9])[N:39]=2)[CH:34]=[CH:33][CH:32]=[CH:31]1
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Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 457859762-(1H-pyrrol-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazoleHCID 117677619Tert-butyl 3-((5-iodo-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

Produkt 1

HCID 117677378(R)-tert-butyl 3-((5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62652Cuprous chlorideKatalysatorHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 40 mL vial chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl)]-palladium(II) (0.023 g, 0.029 mmol), tert-butyl 3-((5-iodo-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate (Compound (21) (0.15 g, 0.289 mmol), 2-(1H-pyrrol-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (0.088 g, 0.318 mmol) and CuCl (0.031 g, 0.318 mmol) were combined. This mixture was then evacuated and backfilled with argon. Then DMF (2.89 ml) and Cs2CO3 (0.376 g, 1.16 mmol) were added to this flask all under argon. This mixture was then heated at 100° C. for 18 h. The mixture was cooled, filtered, diluted with ethyl acetate (mL), washed with water, then dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified via column chromatography. (0-50% EtOAc/hexane) to give the title compound as a white solid. MS (m/z)=542 (M+H).

Aufarbeitung

  1. customThis mixture was then evacuated
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. additiondiluted with ethyl acetate (mL)
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-edfc0df8dce94c6fa712bd82958981d8
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09221809B2

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