2-{[4-(Trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine → 4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

HRID 2389894Notes

Reaction equation

HRID 2389894 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]#[C:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][CH:11]=CN=1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:15][Si:2]([CH3:1])([CH3:14])[C:3]1[CH:11]=[CH:12][N:13]=[C:8]2[O:7][CH2:6][CH2:5][C:4]=12

Participants

3

Reactant 1

HCID 591793882-{[4-(Trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine

Product 1

HCID 591794274-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridineYield 16%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A solution of 2-{[4-(trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine (116 g, 524 mmol) in nitrobenzene (1000 mL) was stirred at 200° C. for 24 hr. The solvent was removed by silica gel column chromatography (ethyl acetate/hexane=13/87→50/50). The residue was diluted with ethyl acetate, and the mixture was extracted twice with 1M hydrochloric acid. The aqueous layer was neutralized with 8M aqueous sodium hydroxide solution and extracted with ethyl acetate. The solvent was evaporated under reduced pressure to give the title compound (16.2 g, yield 14%).

Workup

  1. customThe solvent was removed by silica gel column chromatography (ethyl acetate/hexane=13/87→50/50)
  2. additionThe residue was diluted with ethyl acetate
  3. extractionthe mixture was extracted twice with 1M hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-66e42e340bd64edcb982991f7662555f
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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