Azetidine → 4-(Azetidin-1-yl)-6-chloropyrimidine-5-carbaldehyde

HRID 72708

Reaktionsgleichung

Reaktionsgleichung von HRID 72708
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[NH:11]1[CH2:14][CH2:13][CH2:12]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[N:11]1([C:2]2[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=2)[CH2:14][CH2:13][CH2:12]1

Komponenten

5

Edukt 2

HCID 10422AzetidineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Produkt 1

HCID 867125624-(Azetidin-1-yl)-6-chloropyrimidine-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 4,6-dichloropyrimidine-5-carbaldehyde (1.00 g, 5.65 mmol) in chloroform at 0° C. were added azetidine (99%, 0.392 mL, 5.71 mmol) and triethylamine (5 drops). The reaction mixture was allowed to warm to room temperature and then stirred for 18 hours. The reaction mixture was filtered, and the filtrate was purified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) to provide the product. Yield: 880 mg, 4.45 mmol, 79%. LCMS m/z 198.1, 200.1 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.34-2.43 (m, 2H), 4.12-4.33 (br m, 4H), 8.30 (s, 1H), 10.28 (s, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane)
  3. customto provide the product

Quellen und Nachweise

ORD-Eintrag
ord-50b2e28456f84a5494615235ad31a5bc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829010B2

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