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Sodium hydride → 4-[4-Methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-benzoic acid

HRID 628830
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 628830
CN(C)[C:3]([CH3:17])=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.C([O:23][C:24](=[O:34])[C:25]1[CH:30]=[CH:29][C:28]([C:31](=[NH:33])[NH2:32])=[CH:27][CH:26]=1)(C)(C)C.C(OC(=O)C1C=CC=C(C(=N)N)C=1)(C)(C)C.[H-].[Na+]>C(O)C>[CH3:17][C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=2)[N:32]=[C:31]([C:28]2[CH:27]=[CH:26][C:25]([C:24]([OH:23])=[O:34])=[CH:30][CH:29]=2)[N:33]=1
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Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 570945934-Carbamimidoyl-benzoic acid tert-butyl esterHCID 692346333-Dimethylamino-1-(4-trifluoromethyl-phenyl)-but-2-en-1-oneHCID 692347943-Carbamimidoyl-benzoic acid tert-butyl ester

Produkt 1

HCID 581565134-[4-Methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-benzoic acidAusbeute 2,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Part B. To a mixture of 3-dimethylamino-1-(4-trifluoromethyl-phenyl)-but-2-en-1-one (290.1 mg, 1.13 mmol), 4-carbamimidoyl-benzoic acid tert-butyl ester (220.3 mg, 1.00 mmol, prepared by the same manner as 3-carbamimidoyl-benzoic acid tert-butyl ester) and sodium hydride (79.9 mg, 2.00 mmol, 60% in hexanes) is added dry ethanol (5.0 mL). The resulting mixture is stirred at refluxing for 14 h until complete consumption of the starting material is determined by TLC. The solvent is removed, and the residue is neutralized with 1N HCl until pH <7 to precipitate a white solid, which is collected by filtration followed by washing with water and ethyl ether/hexanes (1:1). The obtained solid is further purified by flash column chromatography, eluting with methanol/methylene chloride (1:40), to give the title product (10.7 mg, 2.7% yield), m.p. 272-275° C. 1H NMR (300 MHz, CDCl3+2 drops DMSO-d6): δ 8.54 (2H, d, J=8.3 Hz), 8.23 (2H, d, J=8.6 Hz), 8.09 (2H, d, J=8.3 Hz), 7.71 (2H, d, J=8.6 Hz), 7.48 (1H, s), 2.61 (3H, s). MS (ES+): m/e 359.27.

Aufarbeitung

  1. temperatureat refluxing for 14 h until complete consumption of the starting material
  2. customThe solvent is removed
  3. customto precipitate a white solid, which
  4. filtrationis collected by filtration
  5. washby washing with water and ethyl ether/hexanes (1:1)
  6. customThe obtained solid is further purified by flash column chromatography
  7. washeluting with methanol/methylene chloride (1:40)

Quellen und Nachweise

ORD-Eintrag
ord-33fc167f10964985bef97ace4419f9de
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315467B2

Notizen zur Reaktion

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