Triethylamine → (R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone

HRID 931318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931318
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.Cl.[NH:13]1[CH2:18][CH2:17][O:16][C@@H:15]([C:19]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH2:14]1.C(N(CC)CC)C>C(#N)C>[NH2:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([N:13]2[CH2:18][CH2:17][O:16][C@@H:15]([C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])[CH2:14]2)[N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 747162-Chloro-5-nitropyrimidin-4-amineHCID 89853903(R)-morpholin-2-yl(pyrrolidin-1-yl)methanone hydrochloride

Produkt 1

HCID 89854246(R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanoneAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Chloro-5-nitropyrimidin-4-amine (106 mg, 0.612 mmol) was added to a solution of (R)-morpholin-2-yl(pyrrolidin-1-yl)methanone hydrochloride (0.15 g, 0.68 mmol) and triethylamine (0.28 mL, 2.04 mmol) in acetonitrile (10 mL) at room temperature. The reaction mixture was heated at 80° C. for 1 h, then was cooled to room temperature and stirred for 12 h. The solvent was removed under reduced pressure and the resulting crude material was triturated with diethyl ether to afford (R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone (0.11 g). MS (ES+APCI) (M+H) 323.1; LCMS retention time: 3.518 min (Method S1).

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting crude material was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-53fa0c8771d746528d4ca7355c52d881
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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