1-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → 1-ethyl-3-(3-fluoro-4-(6-methyl-4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626682
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[CH2:10][N:9]([CH3:11])[CH2:8][C:6]=2[N:7]=1.[CH2:18]([NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[C:26]([F:39])[CH:25]=1)=[O:22])[CH3:19]>>[CH2:18]([NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:3]=[C:4]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:5]3[CH2:10][N:9]([CH3:11])[CH2:8][C:6]=3[N:7]=2)=[C:26]([F:39])[CH:25]=1)=[O:22])[CH3:19]

Komponenten

3

Edukt 2

HCID 666787871-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 866631654-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine2×

Produkt 1

HCID 666791981-ethyl-3-(3-fluoro-4-(6-methyl-4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)ureaAusbeute 26 %

Versuchsvorschrift

Method as example 147 using 4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine (intermediate 21) and 1-ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 28) as starting materials. The crude reaction mixture was partitioned between EtOAc (25 ml) and water (25 ml). The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo. Residue was then purified by prep. HPLC at high pH to afford a light yellow solid (61 mg, 0.15 mmol, 26%).

Aufarbeitung

  1. customThe crude reaction mixture
  2. customwas partitioned between EtOAc (25 ml) and water (25 ml)
  3. customThe organic layer was recovered
  4. customthe solvent removed in vacuo
  5. customResidue was then purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-a8d37baf0e8745089ba1bcd9643cf1ca
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785457B2

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