2,6-Lutidine → HCID 178438602, compound

HRID 2048348Notes

Reaction equation

HRID 2048348 reaction equation
[OH:1][CH2:2][C:3]1([CH2:7][O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([N:15]3[C:20](=[O:21])[C:19]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]5[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:25][CH:24]=4)=[C:18]([CH2:37][CH2:38][CH3:39])[N:17]4[N:40]=[CH:41][N:42]=[C:16]34)[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4]1.N1C(C)=CC=CC=1C.O1CCCC1.FC(F)(F)S(O[Si:62]([C:65]([CH3:68])([CH3:67])[CH3:66])([CH3:64])[CH3:63])(=O)=O>C(OCC)(=O)C>[Si:62]([O:1][CH2:2][C:3]1([CH2:7][O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([N:15]3[C:20](=[O:21])[C:19]([CH2:22][C:23]4[CH:24]=[CH:25][C:26]([C:29]5[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:27][CH:28]=4)=[C:18]([CH2:37][CH2:38][CH3:39])[N:17]4[N:40]=[CH:41][N:42]=[C:16]34)[CH2:11][CH2:10]2)[CH2:4][CH2:5][CH2:6]1)([C:65]([CH3:68])([CH3:67])[CH3:66])([CH3:64])[CH3:63]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 8028TetrahydrofuranHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 178438600HCID 178438600, compound

Product 1

HCID 178438602HCID 178438602, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4′-{[4-(trans-4-{[1-(hydroxymethyl)cyclobutyl]methoxy}cyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.3 g), 2,6-lutidine (0.14 mL) and tetrahydrofuran (10 mL) was added tert-butyl(dimethyl)silyl trifluoromethanesulfonate (0.18 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 (0.31 g, 86%).

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-1fc8ec637b1d4c2ebde073c2fff277ef
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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