Sodium Hydroxide → 7-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-one

HRID 860075Notes

Reaction equation

HRID 860075 reaction equation
COP([CH2:7][C:8](=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:14]=1)(=O)OC.[CH3:30][C:31]1[N:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][N:32]=1.[OH-].[Na+]>C1COCC1>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:15]2[N:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[O:29])[CH:7]=[CH:37][C:34]3[CH:33]=[N:32][C:31]([CH3:30])=[N:36][CH:35]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 58765549{6-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-2-oxo-hexyl}-phosphonic acid dimethyl ester

Product 1

HCID 696664127-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-oneYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-7 (42.8 g, 102 mmol) and 2-methyl-pyrimidine-5-carbaldehyde (12.45 g, 102 mmol) in THF (250 mL) at 0° was added 4M NaOH (26.7 mL, 107 mmol) dropwise. After 15 minutes the ice bath was removed and the mixture stirred for an additional 10 minutes. The solution was diluted with water, extracted with ethyl acetate, and dried (Na2SO4). Following concentration, the residue was triturated with ether to give 27.7 g (61%) of 16-1 as a white solid.

Workup

  1. customAfter 15 minutes the ice bath was removed
  2. additionThe solution was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentration
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-e10e64f11bb14241827c5513198492d7
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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