Diethyl Ether → HCID 178437119, compound

HRID 630152Notes

Reaction equation

HRID 630152 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[CH:7][N:6]=[CH:5][C:4]=1[CH2:11][CH3:12].[SH:13][C:14]1[N:19]=[C:18]([OH:20])[CH:17]=[C:16]([C:21](F)(F)F)[N:15]=1.C(N(CC)CC)C.CCOCC>C(O)C>[CH2:11]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH2:9][CH3:10])[C:3]=1[CH2:2][S:13][C:14]1[N:19]=[C:18]([OH:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)[CH3:12].[CH2:9]([C:8]1[CH:7]=[N:6][CH:5]=[CH:4][C:3]=1[CH2:2][S:13][C:14]1[N:19]=[C:18]([OH:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)[CH3:10]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 595893084-(Bromomethyl)-3,5-diethylpyridineHCID 178516148HCID 178516148, compound

Product 2

HCID 178437119HCID 178437119, compoundHCID 178437123HCID 178437123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of crude 4-(bromomethyl)-3,5-diethylpyridine and 2-sulfanyl-6-(trifluromethyl)pyrimidin-4-ol (0.838 g, 5.89 mmol) in anhydrous ethanol (50 mL) at 0° C. was added triethylamine (3.21 g, 4.42 mL, 31.75 mmol). The reaction mixture was allowed to stir at room temperature overnight. The solvent was evaporated to provide a crude residue. Ether was added to precipitate the triethylamine hydrobromide salt. The solid was filtered and washed with ether several times. The combined ether layers were evaporated, and the crude residue was purified by Combiflash using 0-10% MeOH in dichloromethane to provide 2-{[(3,5-diethylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol and 2-{[(3-ethylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid; 1H NMR (400 MHz, DMSO-d6): δ 1.19 (t, 6H), 2.64 (q, 4H), 4.55 (s, 2H), 6.70 (s, 1H), 8.30 (s, 2H); M+1 344.4.

Workup

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

Sources & evidence

ORD record
ord-4b220a86f14e4f1ab6f1a8a542fb22cd
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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