Triethylamine → HCID 178429459, compound

HRID 630067Notes

Reaction equation

HRID 630067 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:10])=[N:5][CH:6]=[CH:7][C:8]=1[Cl:9].[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1.C(N(CC)CC)C>C(O)C>[Cl:10][C:4]1[C:3]([CH2:2][S:18][C:16]2[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=2)=[C:8]([Cl:9])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 589517013-(Bromomethyl)-2,4-dichloropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429459HCID 178429459, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(bromomethyl)-2,4-dichloropyridine (1.41 g, 5.86 mmol) in anhydrous ethanol (20 mL) was added 6-methyl-2-sulfanylpyrimidin-4-ol (0.58 g, 4.09 mmol) and triethylamine (0.65 g, 6.43 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and water was added to precipitate the product. The white solid was filtered and washed with water and ether to provide 2-{[(2,4-dichloropyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid (0.795 g, 45% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.23 (s, 3H), 2.31 (s, 3H), 4.68 (s, 2H), 6.04 (bs, 1H), 7.67 (d, J=5.3 Hz, 1H), 8.35 (d, J=5.3 Hz, 1H); M+302.3.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. customto precipitate the product
  4. filtrationThe white solid was filtered
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-1981c913e9fd4f90bb211e48604ff71e
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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