Triethylamine → HCID 178429425, compound

HRID 577017Notes

Reaction equation

HRID 577017 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.Br[CH2:11][C:12]1[C:13]([Cl:22])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.C(N(CC)CC)C>C(O)C>[Cl:22][C:13]1[C:12]([CH2:11][S:8][C:6]2[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13593314HCID 13593314, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429425HCID 178429425, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 6-methyl-2-sulfanylpyrimidin-4-ol (0.492 g, 3.46 mmol) and 3-(bromomethyl)-2-chloroquinoline (1.27 g, 4.95 mmol) in anhydrous ethanol (30 mL) at room temperature was added triethylamine (1.50 g, 14.85 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated to dryness and water (50 mL) was added. The mixture was sonicated, and a white solid precipitated out. The product was filtered, washed with water, washed with ether, and then dried in vacuo to provide 2-{[(2-chloroquinolin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid (1.03 g, 66% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.24 (s, 3H), 4.57 (s, 2H), 6.00 (bs, 1H), 7.61 (t, 1H), 7.78 (t, 1H), 7.79 (d, J=10.8 Hz, 1H), 8.01 (d, J=10.8 Hz, 1H), 8.67 (s, 1H); M+ 317.8.

Workup

  1. customThe solvent was evaporated to dryness and water (50 mL)
  2. additionwas added
  3. customThe mixture was sonicated
  4. customa white solid precipitated out
  5. filtrationThe product was filtered
  6. washwashed with water
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-eb10dd4dc69c408e869654401347d585
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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