Diethyl Ether → HCID 178437124, compound

HRID 577104Notes

Reaction equation

HRID 577104 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[CH:7][N:6]=[CH:5][C:4]=1[Cl:11].[SH:12][C:13]1[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([C:20]([F:23])([F:22])[F:21])[N:14]=1.C(N(CC)CC)C.CCOCC>C(O)C>[Cl:11][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH2:9][CH3:10])[C:3]=1[CH2:2][S:12][C:13]1[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([C:20]([F:23])([F:21])[F:22])[N:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 595893674-(Bromomethyl)-3-chloro-5-ethylpyridineHCID 178516148HCID 178516148, compound

Product 1

HCID 178437124HCID 178437124, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of crude 4-(bromomethyl)-3-chloro-5-ethylpyridine (2.5 g, 10.66 mmol), 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (1.35 g, 6.92 mmol) in anhydrous ethanol (50 mL) at 0° C. was added triethylamine (3.77 g, 37.31 mmol). The reaction mixture was allowed to stir overnight at room temperature. The solvent was evaporated to provide a crude residue. Ether was added to precipitate the triethylamine hydrochloride salt. The solid was filtered and washed with ether several times. The combined ether layers were evaporated to provide a crude residue, which was purified by Combiflash using 0-10% MeOH in dichloromethane to provide 2-{[(3-chloro-5-ethylpyridin-4-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol as a white solid (1.5 g, 40% yield); 1H NMR (400 MHz, CDCl3): δ 1.17 (t, 3H), 2.24 (s, 3H), 2.84 (q, 2H), 4.65 (s, 2H), 6.72 (s, 1H), 8.41 (s, 1H), 8.50 (s, 1H); M+ 350.1

Workup

  1. customThe solvent was evaporated
  2. customto provide a crude residue
  3. customto precipitate the triethylamine hydrochloride salt
  4. filtrationThe solid was filtered
  5. washwashed with ether several times
  6. customThe combined ether layers were evaporated
  7. customto provide a crude residue, which
  8. customwas purified by Combiflash

Sources & evidence

ORD record
ord-ea2b50db69964ac2aecf43e73b9c077f
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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