Potassium Carbonate → HCID 57597256, compound

HRID 1787043Notes

Reaction equation

HRID 1787043 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 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 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-4e335dea5f614c4dbccfe0386b8511db
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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