2-Pyrrolidone → HCID 89579872, Verbindung

HRID 928609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928609
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].Cl[CH2:10][C:11]1[N:12]=[C:13]([N:26]2[CH2:31][CH2:30][CH:29]([CH2:32][OH:33])[CH2:28][CH2:27]2)[C:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][S:17][C:15]=2[N:16]=1>CN(C)C=O>[OH:33][CH2:32][CH:29]1[CH2:30][CH2:31][N:26]([C:13]2[C:14]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:18][S:17][C:15]=3[N:16]=[C:11]([CH2:10][N:3]3[CH2:7][CH2:6][CH2:5][C:4]3=[O:8])[N:12]=2)[CH2:27][CH2:28]1

Komponenten

5

Edukt 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 89579974HCID 89579974, Verbindung

Produkt 1

HCID 89579872HCID 89579872, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (25 mg, 60% w/w in mineral oil) was added to a solution of 2-pyrrolidinone in dry N,N-dimethylformamide (2 mL) under a nitrogen atmosphere. The mixture was stirred for 10 min then [1-[2-(chloromethyl)-5-phenyl-thieno[2,3-d]pyrimidin-4-yl]-4-piperidyl]methanol (100 mg) was added. The mixture was stirred for 2 hr at room temperature. The solvent was evaporated and the residue was dissolved in ethyl acetate (10 mL) and water (10 mL). The layers were separated and the aqueous was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (1×10 mL), dried (sodium sulfate), filtered and evaporated to give the target compound (96 mg) as a yellow solid. m/z [M+H]+ 424.0. Retention time 3.95 min (LCMS method+ve 6 min). It was used in the next reaction without purification.

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hr at room temperature
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate (10 mL)
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with ethyl acetate (2×10 mL)
  6. washThe combined organic layers were washed with brine (1×10 mL)
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c4d63b1a195241739c7b5b4d15aaa5e3
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290511B2

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