Diisopropylethylamine → HCID 66589959, Verbindung

HRID 16897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 16897
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[CH2:12]([N:14]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH3:13].C(N(C(C)C)C(C)C)C>ClCCl>[CH2:12]([N:14]1[CH2:20][CH2:19][CH2:18][N:17]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:16][CH2:15]1)[CH3:13]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 75775381-Ethyl-1,4-diazepaneHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Produkt 1

HCID 66589959HCID 66589959, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of methyl 2-chloropyrimidine-5-carboxylate (200 mg, 1.16 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of 1-ethyl-1,4-diazepane (149 mg, 1.16 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.902 mL, 5.22 mmol) in dichloromethane (4.00 mL) at 25° C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (20 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(4-ethyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (268 mg, 87%) as a cream oil which crystallised on standing. This was used directly with no further purification.

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in MeOH (20 mL)
  3. customthe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9bdfa50352ea48c7beff3dbaa7d6e751
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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