Triethylamine → HCID 178429520, compound

HRID 577114Notes

Reaction equation

HRID 577114 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[C:11]=1[Cl:12].[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(N(CC)CC)C>C(O)C>[Cl:12][C:11]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[CH2:2][S:20][C:18]1[N:17]=[C:16]([OH:21])[CH:15]=[C:14]([CH3:13])[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59589453HCID 59589453, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429520HCID 178429520, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-(bromomethyl)-3-chloroimidazo[1,2-a]pyridine (1.07 g, 5.87 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (0.539 g, 3.82 mmol) in anhydrous ethanol (30 mL) at 0° C. was added triethylamine (2.08 g, 2.86 mL, 20.57 mmol), and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated to dryness, and water was added to precipitate the product. The crude product was purified by column chromatography using dichloromethane and methanol (0-10%) to provide 2-[({3-chloroimidazo[1,2-a]pyridin-2-yl}methyl)sulfanyl]-6-methylpyrimidin-4-ol; 1H NMR (400 MHz, DMSO-d6): δ 2.18 (s, 3H), 4.52 (s, 2H), 6.03 (bs, 1H), 7.07 (t, 1H), 7.35 (t, 1H), 7.59 (d, 1H), 8.30 (d, 1H); M+1 279.3.

Workup

  1. customThe solvent was evaporated to dryness, and water
  2. additionwas added
  3. customto precipitate the product
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6c12c296afd34df0816d5aae7c0ee748
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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