Ethyl Acetate → HCID 178440649, compound

HRID 519834Notes

Reaction equation

HRID 519834 reaction equation
[CH2:1]([C:5]1[N:10]2[N:11]=[CH:12][CH:13]=[C:9]2[N:8]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][CH2:21]C(OCC)=O)[CH2:16][CH2:15]2)[C:7](=[O:27])[C:6]=1[CH2:28][C:29]1[CH:30]=[N:31][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]#[N:42])=[CH:33][CH:34]=1)[CH2:2][CH2:3][CH3:4].[CH3:43][Mg]Br.C([O:49][CH2:50][CH3:51])(=O)C>O1CCCC1>[CH2:1]([C:5]1[N:10]2[N:11]=[CH:12][CH:13]=[C:9]2[N:8]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][CH2:21][C:50]([OH:49])([CH3:51])[CH3:43])[CH2:16][CH2:15]2)[C:7](=[O:27])[C:6]=1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]#[N:42])=[N:31][CH:30]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 178418573HCID 178418573, compoundHCID 178440650HCID 178440650, compound

Product 1

HCID 178440649HCID 178440649, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl ({trans-4-[7-butyl-6-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-5-oxopyrazolo[1,5-a]pyrimidin-4(5H)-yl]cyclohexyl}oxy)acetate (0.26 g) in tetrahydrofuran (3 mL) was added dropwise methylmagnesium bromide (1 M tetrahydrofuran solution, 1.4 mL) at 0° C., and the mixture was stirred for 3 hr. To the reaction mixture were added ethyl acetate and then saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.16 g, 63%).

Workup

  1. extractionsaturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-429866f1bab44047a53f99259a56a0e6
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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