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2-Amino-4,6-dichloropyrimidine → HCID 58504602, Verbindung

HRID 2367283
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2367283
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH2:10]([C@@H:12]1[CH2:17][O:16][CH2:15][CH2:14][NH:13]1)[CH3:11].CCN(C(C)C)C(C)C>CC#N>[Cl:8][C:6]1[CH:7]=[C:2]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][C@H:12]2[CH2:10][CH3:11])[N:3]=[C:4]([NH2:9])[N:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 14267783(3R)-3-Ethylmorpholine

Produkt 1

HCID 58504602HCID 58504602, VerbindungAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To 4,6-dichloro-2-pyrimidinamine (240 mg, 1.46 mmol) in CH3CN (8 mL) were added (3R)-3-ethylmorpholine (244 mg, 1.61 mmol) and Hunig's base (1.02 mL, 5.85 mmol), and the reaction mixture was heated in a microwave at 150° C. for a total of 3 hours, checking the progression of the reaction at regular intervals. The mixture was evaporated under vacuum, and the resulting residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×) and CH2Cl2 (2×). The organics were washed with water and brine, dried (MgSO4), filtered and evaporated. The resulting material was triturated with Et2O and dried in vacuo to afford the title compound (307 mg). LC-MS (ES) m/z=243, 245 [M+H]+.

Aufarbeitung

  1. customthe progression of the reaction at regular intervals
  2. customThe mixture was evaporated under vacuum
  3. customthe resulting residue was partitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted with EtOAc (2×) and CH2Cl2 (2×)
  5. washThe organics were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting material was triturated with Et2O
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef93fe14888749f2b221a66b05d35c3e
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08697685B2

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