Triethylamine → 4-Diethoxymethyl-2-hexylsulfanyl-6-trifluoromethyl-pyrimidine

HRID 898125Notes

Reaction equation

HRID 898125 reaction equation
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]#[C:6][C:7](=O)[C:8]([F:11])([F:10])[F:9])[CH3:2].Br.[CH2:17]([S:23][C:24](=[NH:26])[NH2:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(N(CC)CC)C>C1COCC1>[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[N:26]=[C:24]([S:23][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:25]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109770935,5-Diethoxy-1,1,1-trifluoro-pent-3-yn-2-oneHCID 12387367(Hexylsulfanyl)methanimidamide hydrobromide

Product 1

HCID 692932984-Diethoxymethyl-2-hexylsulfanyl-6-trifluoromethyl-pyrimidineYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

5,5-Diethoxy-1,1,1-trifluoro-pent-3-yn-2-one (2 g, 8.9 mmol) and 2-hexyl-isothiourea hydrobromide (2.4 g, 9.8 mmol) were dissolved under nitrogen in THF (20 mL). Then triethylamine (2.7 mL, 19.6 mmol) was added slowly. The reaction was exothermic (40° C.). The suspension was stirred for 4 h at 20° C. The product was extracted with AcOEt, sat. NH4Cl solution, dried and concentrated. The residue was purified by silica gel chromatography in heptane/AcOEt 20:1. One obtained 2.5 g (76%) of a colorless oil. MS: m/z=367 (M+H).

Workup

  1. custom(40° C.)
  2. extractionThe product was extracted with AcOEt, sat. NH4Cl solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography in heptane/AcOEt 20:1

Sources & evidence

ORD record
ord-0ccb4f6ef8da45299b21d54196711381
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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