N-Methoxy-N-methylbenzamide → 2-Anilino4(2-benzoyl-1-isopropylimidazol-5-yl)pyrimidine

HRID 32345

Reaktionsgleichung

Reaktionsgleichung von HRID 32345
C([Li])CCC.[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH:24]([CH3:26])[CH3:25])[C:22]([CH:27]=[O:28])=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CON(C)C(=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH:24]([CH3:25])[CH3:26])[C:22]([C:27](=[O:28])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 113949762-Anilino4(2-benzoyl-1-isopropylimidazol-5-yl)pyrimidineAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

n-Butyllithium (3.12 ml of 1.6 M solution in hexane, 5.0 mmol) was added to a stirred solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 558 mg, 2.0 mmol) in anhydrous THF (20 ml) cooled to −70° C. The mixture was stirred for 30 minutes and then N-methoxy-N-methylbenzamide (660 mg, 4.0 mmol) was added and the reaction mixture was allowed to warm and stirred at ambient temperature for 18 hour. The reaction mixture was quenched with water (20 ml), and extracted with EtOAc (4×25 ml). The organic extracts were washed with brine (2×50 ml), dried and the volatiles removed by evaporation and the residue triturated with ether and the solid collected by filtration to give the title compound (303 mg, 43%) as a pale yellow crystalline solid. NMR (CDCl3): 1.55-1.70 (m, 8H), 5.52-5.68 (sept, 1H), 6.99 (d, 1H), 7.09 (dt, 1H), 7.18 (br s, 1H), 7.30-7.40 (m, 2H), 7.45-7.54 (m, 2H), 7.55 (s, 1H), 7.56-7.62 (m, 3H), 8.09 (d, 2H), 8.49 (d, 1 H); m/z 384.

Aufarbeitung

  1. temperatureto warm
  2. stirringstirred at ambient temperature for 18 hour
  3. customThe reaction mixture was quenched with water (20 ml)
  4. extractionextracted with EtOAc (4×25 ml)
  5. washThe organic extracts were washed with brine (2×50 ml)
  6. customdried
  7. customthe volatiles removed by evaporation
  8. customthe residue triturated with ether
  9. filtrationthe solid collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-484b93adf97c48f698d4757d78117903
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427626B2

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