Ethyl orthoformate → HCID 136337142, compound

HRID 519659Notes

Reaction equation

HRID 519659 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([NH:27][NH2:28])[NH:8][C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH:29](OCC)(OCC)OCC>>[CH2:1]([C:5]1[N:6]2[CH:29]=[N:28][N:27]=[C:7]2[NH:8][C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 136337141HCID 136337141, compound

Product 1

HCID 136337142HCID 136337142, compoundYield 17%

Conditions

Temperature
100 °C

Procedure

A mixture of 4′-[(4-butyl-2-hydrazino-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (2.6 g) and triethyl orthoformate (30 mL) was stirred at 100° C. for 16 hr. The reaction mixture was concentrated, and ethyl acetate and water were added to the obtained residue. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.46 g, 17%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate and water were added to the obtained residue
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-483fd2a0b5b74ff8ac34226d35cd90f7
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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