Triethylamine → HCID 178437801, compound

HRID 577229Notes

Reaction equation

HRID 577229 reaction equation
Br[CH2:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[CH2:8][CH3:9].[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[CH2:8]([C:4]1[N:5]=[CH:6][S:7][C:3]=1[CH2:2][S:17][C:15]1[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 595893325-(Bromomethyl)-4-ethyl-1,3-thiazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178437801HCID 178437801, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(bromomethyl)-4-ethyl-1,3-thiazole (7.0 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (700 mg, 4.9 mmol), and triethylamine (3.0 mL, 21.5 mmol) in absolute ethanol (70 mL) was stirred at room temperature overnight. The mixture was evaporated, and the residue was treated with 50% diethyl ether/acetone (100 mL). The solid material was removed by filtration. The filtrate was recovered and evaporated. The crude product was purified by flash chromatography (0-10% MeOH/CH2Cl2). The column was repeated 4 times, affording the title compound (132 mg, 10% yield); 1H NMR (500 MHz, DMSO-d6): δ 1.19 (t, 2H, J=7.5 Hz), 2.801 (m, 2H, J=7.5 Hz), 4.55 (s, 2H), 6.05 (s, 1H), 8.85 (s, 1H); M+ 268.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was treated with 50% diethyl ether/acetone (100 mL)
  3. customThe solid material was removed by filtration
  4. customThe filtrate was recovered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cb308a735d994c498de5b067f332afad
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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