Thiobenzamide → 2-Phenyl-4-(2-phenylpyrimidin-5-yl)thiazole

HRID 2274498Notes

Reaction equation

HRID 2274498 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9][CH:10]=1)=O.[C:17]([NH2:25])(=[S:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:18]1([C:17]2[S:24][CH:2]=[C:3]([C:5]3[CH:6]=[N:7][C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][CH:10]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 592524542-Bromo-1-(2-phenylpyrimidin-5-yl)ethanone

Product 1

HCID 592524472-Phenyl-4-(2-phenylpyrimidin-5-yl)thiazoleYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 2-bromo-1-(2-phenylpyrimidin-5-yl)ethanone (Example 14, Step B, 50 mg, 0.18 mmol), thiobenzamide (TCI America, 25 mg, 0.18 mmol) and absolute ethanol (4 mL) in a capped scintillation vial was heated to near boiling for several minutes and was subsequently allowed to cool to room temperature. A white solid precipitated within minutes. The precipitate was collected by vacuum filtration. Light ethanol rinse, suction, and drying under high vacuum at room temperature afforded the title compound (26 mg, 46% yield) as an off-white solid; melting point 214.4-216.1° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.54 (s, 2H), 8.54 (s, 1H), 8.47 (m, 2H), 8.08 (m, 2H), 7.62-7.54 (m, 6H); LC/MS (ESI+) m/z 316.1, (ESI−) m/z 337.2 (M−1+Na+); H-PGDS FPBA IC50: >20 μM.

Workup

  1. temperaturewas heated
  2. waitto near boiling for several minutes
  3. customA white solid precipitated within minutes
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washLight ethanol rinse
  6. customsuction, and drying under high vacuum at room temperature

Sources & evidence

ORD record
ord-d82e5b6d750647f381d622fb4d374944
Source dataset
uspto-grants-2015_09
Patent number
US09126973B2

Reaction notes

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