Sodium Bicarbonate → HCID 59491430, compound

HRID 577417Notes

Reaction equation

HRID 577417 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([S:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24](OC)=[O:25])[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>O1CCCC1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([S:20][C:21]4[CH:22]=[C:23]([CH2:24][OH:25])[CH:28]=[CH:29][CH:30]=4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 59491480HCID 59491480, compound

Product 1

HCID 59491430HCID 59491430, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred mixture of methyl 3-(2-(4-morpholinophenylamino)pyrimidin-4-ylthio)benzoate (4.00 g, 9.46 mmol) in anhydrous tetrahydrofuran, was added lithium aluminum hydride (360 mg, 9.46 mmol) in small portions while the mixture was gently warmed to 40° C. The mixture was stirred at this temperature for about 4 hours. It was then cooled on an ice bath, cold 10% aqueous sodium bicarbonate solution was added slowly to quench the reaction. The whole mixture was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution. The aqueous layer was re-extracted with ethyl acetate. The combined organic layer was washed with brine, dried (Na2SO4). Removal of the solvent in vacuo afforded the product (2.50 g, 80%).

Workup

  1. temperatureIt was then cooled on an ice bath
  2. customto quench
  3. customthe reaction
  4. customThe whole mixture was partitioned between ethyl acetate and 10% aqueous sodium bicarbonate solution
  5. extractionThe aqueous layer was re-extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-3a42efce93af4a2cbe060ef1aafd7d1f
Source dataset
uspto-grants-2015_05
Patent number
US09040549B2

Reaction notes

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