Triethylamine → HCID 178429437, compound

HRID 577195Notes

Reaction equation

HRID 577195 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]O)=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.BrP(Br)Br.[CH3:15][C:16]1[N:21]=[C:20]([SH:22])[N:19]=[C:18]([OH:23])[CH:17]=1.C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[C:7]([CH2:8][S:22][C:20]2[N:19]=[C:18]([OH:23])[CH:17]=[C:16]([CH3:15])[N:21]=2)=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24614Phosphorus tribromideHCID 103293512,4-Dimethyl-3-pyridinemethanolHCID 178429541HCID 178429541, compound

Product 1

HCID 178429437HCID 178429437, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2,4-dimethylpyridin-3-yl)methanol was dissolved in dichloromethane (100 mL). Tribromophosphane (1.5 mL, 16 mmol) was added slowly. After 2 hours, the mixture was evaporated to dryness. The crude solid was dissolved in cold ethanol (100 mL), and 6-methyl-2-sulfanylpyrimidin-4-ol (1.13 g, 8.0 mmol) and triethylamine (4.5 mL, 32 mmol) were added. The resulting mixture was stirred at room temperature for 3 hours. The solvent was evaporated, and the crude solid was washed with THF (200 mL). After evaporation of solvent, the crude was purified by CombiFlash (0-6% MeOH in DCM) to provide 2-{[(2,4-dimethylpyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (2.5 g, 64% yield); 1H NMR (500 MHz, DMSO-d6): δ 2.23 (s, 3H), 2.68 (s, 3H), 2.84 (s, 3H), 4.62 (s, 2H), 6.05 (br, 1H), 7.71 (s, 1H), 8.62 (s, 1H); M+ 232.

Workup

  1. customthe mixture was evaporated to dryness
  2. dissolutionThe crude solid was dissolved in cold ethanol (100 mL)
  3. customThe solvent was evaporated
  4. washthe crude solid was washed with THF (200 mL)
  5. customAfter evaporation of solvent
  6. customthe crude was purified by CombiFlash (0-6% MeOH in DCM)

Sources & evidence

ORD record
ord-24bd45339ce04bd4967a1437bf2ff7b0
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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