Diethyl Ether → HCID 178437119, compound

HRID 577110Notes

Reaction equation

HRID 577110 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-(trifluoromethyl)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-f82a7afbc67e49ebbd3530fbb55c37cb
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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