Triethylamine → HCID 178429442, compound

HRID 630235Notes

Reaction equation

HRID 630235 reaction equation
Br[CH2:2][C:3]1[C:4]([C:9]([F:12])([F:11])[F:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(N(CC)CC)C>C(O)C>[CH3:13][C:14]1[N:19]=[C:18]([S:20][CH2:2][C:3]2[C:4]([C:9]([F:12])([F:11])[F:10])=[N:5][CH:6]=[CH:7][CH:8]=2)[N:17]=[C:16]([OH:21])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 534172483-(BroMoMethyl)-2-(trifluoroMethyl)pyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429442HCID 178429442, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of crude 3-(bromomethyl)-2-(trifluoromethyl)pyridine (0.684 g, 2.84 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (0.242 g, 1.70 mmol) in anhydrous ethanol (100 mL) at 0° C. was added triethylamine (1.14 g, 1.57 mL, 11.36 mmol). The reaction mixture was allowed to stir at room temperature overnight. The solvent was evaporated, and ether was added to the precipitated triethylamine hydrobromide salt. The solid was filtered and washed with ether several times. The solvent was evaporated to provide a crude residue, which was purified by Combiflash using 0-10% MeOH:dichloromethane. 6-methyl-2-({[2-(trifluoromethyl)pyridin-3-yl]methyl}sulfanyl)pyrimidin-4-ol was obtained as a white solid (0.438 g, 51% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.14 (t, 3H), 2.21 (s, 3H), 2.61 (q, 2H), 4.35 (s, 2H), 6.00 (bs, 1H), 7.69 (s, 1H), 8.31 (s, 1H), 8.45 (s, 1H); M+301.5.

Workup

  1. customThe solvent was evaporated
  2. additionether was added to the precipitated triethylamine hydrobromide salt
  3. filtrationThe solid was filtered
  4. washwashed with ether several times
  5. customThe solvent was evaporated
  6. customto provide a crude residue, which
  7. customwas purified by Combiflash

Sources & evidence

ORD record
ord-4e8a47f90ceb4b9dbf1ae23c544798bd
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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