Sodium Hydroxide → HCID 56834577, compound

HRID 385662Notes

Reaction equation

HRID 385662 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:33]5[N:34]=[C:35]([O:38][CH3:39])[N:36]=[CH:37][C:32]=5[CH:31]=[CH:30][C:29]4=[O:40])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+]>ClCCl.FC(F)(F)C(O)=O>[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:33]5[N:34]=[C:35]([O:38][CH3:39])[N:36]=[CH:37][C:32]=5[CH:31]=[CH:30][C:29]4=[O:40])[CH2:22][CH2:21]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57815495HCID 57815495, compound

Product 1

HCID 56834577HCID 56834577, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 0.54 g of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(2-methoxy-7-oxopyrido(2,3-d)pyrimidin-8(7H)-yl)ethyl)piperidin-4-yl)carbamate in 15 mL of dichloromethane, 5 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 2 hours. A 2 mol/L aqueous sodium hydroxide solution was added under cooling with ice to adjust pH at 13, dichloromethane was added thereto, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using an eluent of chloroform:methanol=10:1 to obtain 0.34 g of 8-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-2-methoxypyrido(2,3-d)pyrimidin-7(8H)-one as a yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-ddba6c8b605744c0a1c7d56ffe3a638d
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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