Triethylamine → HCID 178467477, compound

HRID 630285Notes

Reaction equation

HRID 630285 reaction equation
Br[CH2:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[C:8](=[O:10])[CH3:9].[SH:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=1.C(N(CC)CC)C>C(O)C>[C:8]([C:4]1[N:5]=[CH:6][S:7][C:3]=1[CH2:2][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:20])[F:21])[N:13]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59589488HCID 59589488, compoundHCID 178516148HCID 178516148, compound

Product 1

HCID 178467477HCID 178467477, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-[5-(bromomethyl)-1,3-thiazol-4-yl]ethan-1-one (615 mg, 2.8 mmol) and 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (255 mg, 1.3 mmol) in absolute ethanol (25 mL) at 0° C. was added triethylamine (725 μL, 5.2 mmol). The mixture was stirred at room temperature for 4 hours. The mixture was evaporated, and the solid residue was treated with diethyl ether (50 mL). The solid salts were removed by filtration. The filtrate was recovered and evaporated. The crude product was purified by flash chromatography (0-10% MeOH/CH2Cl2 and 0-5% MeOH/CH2Cl2), affording 2-{[(4-acetyl-1,3-thiazol-5-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (150 mg, 34%); 1H NMR (500 MHz, DMSO-d6): δ 2.71 (s, 3H), 4.82 (s, 2H), 6.58 (s, 1H), 8.99 (s, 1H); M+336.

Workup

  1. customThe mixture was evaporated
  2. additionthe solid residue was treated with diethyl ether (50 mL)
  3. customThe solid salts were removed by filtration
  4. customThe filtrate was recovered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (0-10% MeOH/CH2Cl2 and 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-07314fdb0b76496680e8526ae25d2931
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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