Hydrochloric Acid → HCID 178493736, compound

HRID 577258Notes

Reaction equation

HRID 577258 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Cl)[C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[N:11]=1.[CH3:22][O-:23].[Na+].O.Cl>CS(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:23][CH3:22])[C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[N:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 178516146HCID 178516146, compound

Product 1

HCID 178493736HCID 178493736, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-6-(trifluoromethyl)-pyrimidin-4-ol (see, e.g., Example 120; 1.0 g, 2.8 mmol) and a sodium methoxide solution (25% wt., 2.6 mL) in dimethyl sulfoxide (10 mL) was stirred at 70° C. overnight. Water (100 mL) was added, and the pH of the mixture was adjusted to around 6 with 2N HCl. The mixture was extracted with EtOAc (3×75 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo to afford 2-{[(3-chloro-5-methoxypyridin-4-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (912 mg. 93%); 1H NMR (500 MHz, DMSO-d6): δ 3.97 (s, 3H), 4.59 (s, 2H), 6.68 (s (br), 1H), 8.32 (s, 1H), 8.39 (s, 1H); M+ 352.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×75 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8983348696494b88bd236d14c93655fa
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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