Ethanol → (3-(((2-Amino-6-chloro-4-pyrimidinyl)amino)methyl)-3-oxetanyl)methanol

HRID 1421872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421872
[NH2:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1.[NH2:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[N:11]=1.C(O)C>C(N(CC)CC)C>[NH2:9][C:10]1[N:15]=[C:14]([NH:1][CH2:2][C:3]2([CH2:7][OH:8])[CH2:6][O:5][CH2:4]2)[CH:13]=[C:12]([Cl:17])[N:11]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 655222-Amino-4,6-dichloropyrimidineHCID 18706850[3-(Aminomethyl)oxetan-3-yl]methanol

Produkt 1

HCID 385214(3-(((2-Amino-6-chloro-4-pyrimidinyl)amino)methyl)-3-oxetanyl)methanolAusbeute 32,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 3-aminomethyl-3-hydroxymethyloxetane (1.17 g, 0.01 mol), 2-amino-4,6-dichloropyrimidine (1.64 g, 0.01 mol), ethanol (40 ml) and triethylamine (4 ml) was refluxed for one day. The solvent was distilled away under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1, later 10:1) to give colorless prism crystals (0.8 g, 32.8%), m.p. 185-186° C. (acetone).

Aufarbeitung

  1. temperaturewas refluxed for one day
  2. distillationThe solvent was distilled away under reduced pressure and ethyl acetate
  3. additionwas added to the residue
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform

Quellen und Nachweise

ORD-Eintrag
ord-efe1ab6d86274af3afad69431d791d0c
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06080750

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