Butyl glycidyl ether → HCID 59151333, Verbindung

HRID 888955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888955
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[C:13]4[S:18][C:17]([CH2:19][N:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:32]([O:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:33]1[O:35][CH2:34]1>CN(C)C=O>[CH2:37]([O:36][CH2:32][CH:33]([OH:35])[CH2:34][N:23]1[CH2:22][CH2:21][N:20]([CH2:19][C:17]2[S:18][C:13]3[C:12]([N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[N:11][C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[C:9]5[C:4]=4[CH:3]=[CH:2][NH:1]5)=[N:15][C:14]=3[CH:16]=2)[CH2:25][CH2:24]1)[CH2:38][CH2:39][CH3:40]

Komponenten

4

Edukt 2

HCID 17049Butyl glycidyl ether2×HCID 11517696HCID 11517696, Verbindung

Produkt 1

HCID 59151333HCID 59151333, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(1H-indol-4-yl)-4-morpholin-4-yl-6-piperazin-1-ylmethyl-thieno[3,2-d]pyrimidine (50 mg) in N,N-dimethylformamide (3 mL) at r.t. was added 0.1 M Na2HPO4pH 6.8 buffer (0.5 mL) and butyl glycidyl ether (18 μL) and the resulting cloudy mixture was heated at 55° C. for 3 days with 2 extra equivalents of butyl glycidyl ether (18 μL) added during this time. The reaction mixture was partitioned between EtOAc (15 mL) and brine (15 mL), the organic layer was dried (Na2SO4), concentrated and the residue purified by flash chromatography (silica; 96:4 EtOAc/MeOH as eluent) to give an off-white solid (38 mg).

Aufarbeitung

  1. additionadded during this time
  2. customThe reaction mixture was partitioned between EtOAc (15 mL) and brine (15 mL)
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography (silica; 96:4 EtOAc/MeOH as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-9bac82cec88a488f90271ea183a73140
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252792B2

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