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

HRID 2096340Notes

Reaction equation

HRID 2096340 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-21061a6d4e6a44ca98fc65f198714196
Source dataset
uspto-grants-2013_05
Patent number
US08450326B2

Reaction notes

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