Triethylamine → [(S)-1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-pyrrolidin-2-yl]-methanol

HRID 334142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 334142
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[C:4](Cl)[N:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:17][OH:18].C(N(CC)CC)C>>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:17][OH:18])[C:5]([O:9][CH3:10])=[C:6]([Cl:8])[N:7]=1

Komponenten

4

Edukt 3

HCID 8471TriethylamineHCID 640091L-ProlinolHCID 202711362,4,6-Trichloro-5-methoxypyrimidine

Produkt 1

HCID 86667360[(S)-1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-pyrrolidin-2-yl]-methanolAusbeute 70 %

Versuchsvorschrift

A mixture of 2,4,6-trichloro-5-methoxy-pyrimidine (1.2 g, 5.62 mmol), (S)-1-pyrrolidin-2-yl-methanol (1.1 mL, 11.3 mmol) and triethylamine (1.08 mL, 7.75 mmol) in IMS (36 mL) was stirred at RT for 20 mins, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 0 to 50% ethyl acetate in cyclohexane) affording [(S)-1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-pyrrolidin-2-yl]-methanol (1.08 mg, 70%). LCMS (method A): RT=2.98 min, [M+H]+=278/280.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, 0 to 50% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-6751090918cd4b95a17335f90c3bbd20
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883799B2

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