Triethylamine → 1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanol

HRID 898133Notes

Reaction equation

HRID 898133 reaction equation
O[CH:2]([CH3:8])[C:3]#[C:4][C:5](=[O:7])[CH3:6].Br.[CH2:10]([S:16][C:17](=[NH:19])[NH2:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(N(CC)CC)C>C1COCC1>[CH2:10]([S:16][C:17]1[N:19]=[C:4]([CH:5]([OH:7])[CH3:6])[CH:3]=[C:2]([CH3:8])[N:18]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108986755-Hydroxy-3-hexyn-2-oneHCID 12387367(Hexylsulfanyl)methanimidamide hydrobromide

Product 1

HCID 692907201-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanolYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Hydroxy-hex-3-yn-2-one (2 g, 18 mmol) and 2-hexyl-isothiourea hydrobromide (5.2 g, 21 mmol) were dissolved in THF (10 mL). Then the triethylamine (5.5 mL, 40 mmol) was added and stirring continued for 3 h. The reaction was slightly exothermic. The mixture was extracted with AcOEt and sat. NH4Cl solution. The crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient. One obtained 2.8 g (61%) of a light yellow oil. MS: m/z=254 (M)

Workup

  1. extractionThe mixture was extracted with AcOEt and sat. NH4Cl solution
  2. customThe crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient

Sources & evidence

ORD record
ord-ed720e50adf24ada9468f6f2da1ed40f
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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