Triethylamine → HCID 178429486, compound

HRID 630011Notes

Reaction equation

HRID 630011 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(N(CC)CC)C.Br[CH2:18][C:19]1[C:24]([F:25])=[CH:23][N:22]=[CH:21][C:20]=1[F:26]>C(O)C>[F:26][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([F:25])[C:19]=1[CH2:18][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668150974-(Bromomethyl)-3,5-difluoropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429486HCID 178429486, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (227 mg, 1.6 mmol) was dissolved in absolute ethanol (20 mL), then triethylamine (335 μL, 2.4 mmol) and 4-(bromomethyl)-3,5-difluoropyridine (350 mg, 1.7 mmol) were added. The mixture was stirred overnight at room temperature. The solvent was removed by evaporation. The residue was triturated in methanol, filtered, washed with water plus diethyl ether, and then dried in vacuo to afford to 2-{[(3,5-difluoropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (179 mg, 42% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.15 (s, 3H), 4.45 (s, 2H), 6.01 (bs, 1H), 8.49 (s, 2H); LRMS (ES+) m/z 270 (100%, M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. customThe residue was triturated in methanol
  3. filtrationfiltered
  4. washwashed with water plus diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c7ff808934914c789d8566df4b266981
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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