2,6-Lutidine → HCID 67008700, compound

HRID 1688405Notes

Reaction equation

HRID 1688405 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:38])[CH2:9][N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)=[C:13]([CH2:32][CH2:33][CH3:34])[N:12]3[N:35]=[CH:36][N:37]=[C:11]23)=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.O1CCCC1.FC(F)(F)S(O[Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])(=O)=O>C(OCC)(=O)C>[Si:58]([O:38][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)=[C:13]([CH2:32][CH2:33][CH3:34])[N:12]2[N:35]=[CH:36][N:37]=[C:11]12)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 8028TetrahydrofuranHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 67009846HCID 67009846, compound

Product 1

HCID 67008700HCID 67008700, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4′-({4-[2-(4-fluorophenyl)-2-hydroxyethyl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.78 g), 2,6-lutidine (0.27 mL) and tetrahydrofuran (20 mL) was added tert-butyl(dimethyl)silyl trifluoromethanesulfonate (0.53 mL), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium hydrogensulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.56 g, 58%).

Workup

  1. washwashed with saturated aqueous potassium hydrogensulfate solution
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a6bbcecb4edc4d4a870d790d19e82f1f
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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