Triethylamine → HCID 178429460, compound

HRID 629982Notes

Reaction equation

HRID 629982 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]([Cl:25])=[CH:23][N:22]=[CH:21][C:20]=1[Cl:26]>C(O)C>[Cl:26][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([Cl: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 222277664-(Bromomethyl)-3,5-dichloropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429460HCID 178429460, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (134 mg, 940 μmol) was dissolved in absolute ethanol (10 mL), then triethylamine (200 μL, 1.4 mmol) and 4-(bromomethyl)-3,5-dichloropyridine (250 mg, 1.0 mmol) were added. The mixture was stirred for 2 hours at room temperature. The solid was removed by filtration, and filtrate was evaporated. The residue was triturated in diethyl ether, filtered, washed with water plus diethyl ether, and then dried in vacuo to afford to 2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (56 mg, 20% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.23 (s, 3H), 4.69 (s, 2H), 6.10 (bs, 1H), 8.66 (s, 2H); LRMS (ES+) m/z 302 (100%, M+1), 304 (70%, M+3).

Workup

  1. customThe solid was removed by filtration, and filtrate
  2. customwas evaporated
  3. customThe residue was triturated in diethyl ether
  4. filtrationfiltered
  5. washwashed with water plus diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a4c172582c6e4ccd8963ecf41b0a12d3
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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