Triethylamine → HCID 178437803, compound

HRID 630291Notes

Reaction equation

HRID 630291 reaction equation
Br.Br[CH2:3][C:4]1[S:8][CH:7]=[N:6][C:5]=1[CH:9]=[CH2:10].[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>[CH:9]([C:5]1[N:6]=[CH:7][S:8][C:4]=1[CH2:3][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)=[CH2:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66820733HCID 66820733, compoundHCID 178516148HCID 178516148, compound

Product 1

HCID 178437803HCID 178437803, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. mixture of 5-(bromomethyl)-4-ethenyl-1,3-thiazole hydrobromide (2.6 mmol) and 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (275 mg, 1.4 mmol) in absolute ethanol (15 mL) was added triethylamine (1.5 mL, 10.8 mmol). The mixture was stirred at room temperature overnight. The solution was evaporated, and the residue was treated with diethyl ether (100 mL). The solid material was removed by filtration. The filtrate was evaporated, and the crude product was purified by flash chromatography (0-5% MeOH/DCM), affording 2-{[(4-ethenyl-1,3-thiazol-5-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (270 mg, 60%); 1H NMR (500 MHz, DMSO-d6): δ 4.75 (s, 2H), 5.42 (dd, 1H, J=2.3 Hz, 10.8 Hz), 6.06 (dd, 1H, J=2.3 Hz, 16.9 Hz), 6.68 (s, 1H), 8.95 (s, 1H); M+320.

Workup

  1. customThe solution was evaporated
  2. additionthe residue was treated with diethyl ether (100 mL)
  3. customThe solid material was removed by filtration
  4. customThe filtrate was evaporated
  5. customthe crude product was purified by flash chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-e1383858a5724c368fa805b9ccd00846
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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