Triethylamine → HCID 178429486, compound

HRID 576970Notes

Reaction equation

HRID 576970 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-460ef5d23c6143119cac16afec31abf9
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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