Water → HCID 57504246, Verbindung

HRID 1097980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097980
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[OH:11][CH:12]([CH2:23][O:24][CH3:25])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=1)=[O:14].Cl[C:27]1[N:32]=[CH:31][N:30]=[C:29]2[N:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])[N:34]=[CH:35][C:28]=12.O>C1COCC1.CCOC(C)=O>[Cl:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[N:33]1[C:29]2=[N:30][CH:31]=[N:32][C:27]([O:11][CH:12]([CH2:23][O:24][CH3:25])[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=3)=[O:14])=[C:28]2[CH:35]=[N:34]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 2733832Lithium Hexamethyldisilazide2×HCID 112655704-Chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-D]pyrimidineHCID 57438612HCID 57438612, Verbindung

Produkt 1

HCID 57504246HCID 57504246, VerbindungAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

LHMDS (1.40 mL, 1.0 M in THF, 1.40 mmol) was added slowly to a stirred solution of 2-hydroxy-3-methoxy-N-(5-methylpyridin-2-yl)propanamide (200 mg, 0.951 mmol) in anhydrous THF (5 mL). The reaction mixture was kept at ambient temperature for 10 minutes, and a solution of 4-chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine (265 mg, 1.00 mmol) in anhydrous THF (3 mL) was added. The reaction mixture was heated at 50° C. for ½ hrs (another 3 equivalents of LHMDS were added and the reaction heated for 18 hrs at 50° C. in example 49). Water and EtOAc were added, and the two phases were separated. The organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:2/1) to give the title compound as a colourless solid (323 mg), 1H NMR (500 MHz, CDCl3) δ 8.67 (br s, 1H), 8.62 (s, 1H), 8.48 (s, 1H), 8.18 (d, 1H), 8.12 (s, 1H), 7.65 (d, 1H), 7.52 (m, 4H), 6.13 (t, 1H), 4.14 (m, 2H), 4.06 (m, 1H), 3.49 (s, 3H), 2.32 (s, 3H), HRMS: calcd for (M+H+) C21H2035ClN6O3: 439.1285. Found: 439.1287.

Aufarbeitung

  1. additionwere added
  2. customthe two phases were separated
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:2/1)

Quellen und Nachweise

ORD-Eintrag
ord-06bfb32d916c4c68b7f421cc7f2e0dbb
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143263B2

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