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

HRID 42306

Reaction equation

HRID 42306 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 (TCl 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-59b63460ac33409aa614d4fadb29ae68
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Linked notes

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