Diisopropylethylamine → Methyl 2-(4-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate

HRID 16906

Reaktionsgleichung

Reaktionsgleichung von HRID 16906
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[CH3:12][N:13]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:12][N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Produkt 1

HCID 66589654Methyl 2-(4-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylateAusbeute 94,4 %

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-methyl-1,4-diazepane (0.144 mL, 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-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (274 mg, 94%) as a white solid. 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-4ab41f61fa5e4209bcc6a4c7197a6667
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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