Tetrahydrofuran → HCID 19017756, compound

HRID 1728339Notes

Reaction equation

HRID 1728339 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([S:13][CH3:14])[N:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O1[CH2:29][CH2:28][CH2:27][CH2:26]1.ICCCC>CN(C)C=O.C(OCC)(=O)C>[CH2:26]([NH:1][C:2]1[N:3]=[C:4]([S:13][CH3:14])[N:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10962Butyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 12318256HCID 12318256, compound

Product 1

HCID 19017756HCID 19017756, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To ethyl 4-amino-1-methyl-2-(methylthio)imidazole-5-carboxylate (3.014 g, 14.00 mmol), prepared by the method of Gompper et al., Tetrahedron Lett. 1885 (1966), in dimethylformamide (50 mL) at 0° C. was added a solution of 1.0M sodium bis(trimethylsilyl)amide in tetrahydrofuran (14.0 mL, 14.0 mmol). After 1 hour, 1-iodobutane (1.75 mL, 15.4 mmol) was added and the reaction was stirred at ambient temperature for 18 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. Chromatography of the residue on silica gel eluting with 5% ethyl acetate in hexane afforded 2.706 g (71%) of the desired product as an oil. TLC (10% ethyl acetate/90% hexane) Rf =0.24. 1H NMR (CDCl3, 300 MHz) d 0.94 (t, 3H), 1.34 (t, 3H), 1.35-1.65 (m, 4H), 2.62 (s, 3H), 3.38-3.49 (m, 2H), 3.66 (s, 3H), 4.28 (q, 2H), 5.58 (br s, 1H). MS (DCl/NH3) m/e 272 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4ee4b6191e8f4afda931478e490cefb1
Source dataset
uspto-grants-1994_07
Patent number
US05326776

Reaction notes

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