Potassium Carbonate → HCID 57597256, compound

HRID 1926129Notes

Reaction equation

HRID 1926129 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[Cl:15][C:16]1[CH:17]=[C:18]([NH:33][C:34]2[C:35]3[N:42]([CH2:43][C:44]#[C:45][CH2:46][OH:47])[CH:41]=[CH:40][C:36]=3[N:37]=[CH:38][N:39]=2)[CH:19]=[CH:20][C:21]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:15][C:16]1[CH:17]=[C:18]([NH:33][C:34]2[C:35]3[N:42]([CH2:43]/[CH:44]=[CH:45]/[CH2:46][OH:47])[CH:41]=[CH:40][C:36]=3[N:37]=[CH:38][N:39]=2)[CH:19]=[CH:20][C:21]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 57597200HCID 57597200, compound

Product 1

HCID 57597256HCID 57597256, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

70% Sodium bis(2-methoxyethoxy)aluminum hydride in toluene solution (0.8 mL) was dissolved in tetrahydrofuran (4 mL), and the solution was cooled to 0° C. A solution of 4-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]but-2-yn-1-ol (262.4 mg) in tetrahydrofuran (10 mL) was added dropwise, and the mixture was stirred at 0° C. for 2 hrs. To the reaction mixture was added 10% aqueous potassium carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=33:67→0:100) and crystallized from hexane/ethyl acetate to give the title compound (195.9 mg) as white crystals.

Workup

  1. extractionthe 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 under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=33:67→0:100)
  7. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-05de3bb5fcda4bee93f0c33afb0ab1c9
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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