Methanol → 2-(3-chlorophenyl)-6-cyclopropylpyrimidin-4(3H)-one

HRID 1508910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508910
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].[CH:11]1([C:14](=O)[CH2:15][C:16](OCC)=[O:17])[CH2:13][CH2:12]1.C[O-].[Na+].CO>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:6][C:16](=[O:17])[CH:15]=[C:14]([CH:11]3[CH2:13][CH2:12]3)[N:7]=2)[CH:8]=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 2041443-Chloro-benzamidineHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 10942334Sodium Methoxide

Produkt 1

HCID 1359755402-(3-chlorophenyl)-6-cyclopropylpyrimidin-4(3H)-oneAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 500-mL round bottomed flask was charged with 3-chlorobenzimidamide (5.75 g, 30.1 mmol), ethyl 3-cyclopropyl-3-oxopropanoate (5.00 g, 32.0 mmol), and ethanol (100 mL) and the mixture cooled to 0° C. To the stirred mixture was added 25% sodium methoxide in methanol (15.0 mL, 64.0 mmol). The resulting mixture was stirred at reflux for 20 h. After cooling to room temperature, the mixture was evaporated under reduced pressure to 25 mL. The residual slurry was cautiously treated with 2N HCl (50 mL) forming a solid. The solid was collected by filtration and washed with water followed by ether to afford the title compound (2.46 g, 31%) as a white solid, which was carried forward into the next step without further purification. MW=246.69. 1H NMR (DMSO-d6, 500 MHz) δ 12.55 (s, 1H), 8.13 (s, 1H), 8.06 (d, J=7.5 Hz, 1H), 7.64-7.60 (m, 1H), 7.54 (t, J=8.0 Hz, 1H), 6.34 (s, 1H), 2.00-1.93 (m, 1H), 1.08-1.02 (m, 2H), 0.99-0.91 (m, 2H).

Aufarbeitung

  1. temperatureat reflux for 20 h
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was evaporated under reduced pressure to 25 mL
  4. additionThe residual slurry was cautiously treated with 2N HCl (50 mL)
  5. customforming a solid
  6. filtrationThe solid was collected by filtration
  7. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-d9260cf37cde46febc80d0b25d151003
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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