Sodium hydride → 3-[4-(4-Fluoro-phenyl)-pyrimidin-2-yl]-benzoic acid

HRID 628829Notes

Reaction equation

HRID 628829 reaction equation
C([O:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[NH:15])[NH2:14])[CH:8]=1)(C)(C)C.CN([CH:20]=[CH:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=O)C.[H-].[Na+]>C(O)C>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]2[CH:21]=[CH:20][N:14]=[C:13]([C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([OH:5])=[O:16])[N:15]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6005393-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-oneHCID 692347943-Carbamimidoyl-benzoic acid tert-butyl ester

Product 1

HCID 115366593-[4-(4-Fluoro-phenyl)-pyrimidin-2-yl]-benzoic acidYield 49.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part B. To a mixture of 3-carbamimidoyl-benzoic acid tert-butyl ester (220.2 mg, 0.94 mmol), 3-dimethylamino-1-(4-fluoro-phenyl)-propenone (182.6 mg, 0.95 mmol) and sodium hydride (39.2 mg, 1.63 mmol, 60% in hexanes) is added dry ethanol (5.0 mL). The resulting mixture is stirred at refluxing for 8 h until complete consumption of the starting material as determined by TLC. The solvent is removed, and the residue is added to 1N HCl (15 mL) to precipitate a yellow solid. The title product (137.8 mg, 41.3% yield) is produced after washing with water, then ethyl ether in sequence, m.p. 239-241° C. 1H NMR (300 MHz, DMSO-d6): δ 9.05 (1H, s), 8.97 (1H, d, J=5.0 Hz), 8.73 (1H, dd, J=7.7, 1.2 Hz), 8.38 (2H, m), 8.11 (1H, dd, J=8.0, 1.2 Hz), 8.04 (1H, d, J=5.3 Hz), 7.68 (1H, t, J=7.8 Hz), 7.43 (2H, m). MS (ES+): m/e 295.27.

Workup

  1. temperatureat refluxing for 8 h until complete consumption of the starting material
  2. customThe solvent is removed
  3. additionthe residue is added to 1N HCl (15 mL)
  4. customto precipitate a yellow solid

Sources & evidence

ORD record
ord-0988fea8368543a7b8395bed8041ce45
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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