Triethylamine → HCID 67955046, compound

HRID 1846398Notes

Reaction equation

HRID 1846398 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:5][CH:4]=[C:3]1[C:20]([OH:22])=[O:21].[I-].ClC1C=CC=C[N+]=1C.[C:32]1(=O)[CH2:37][CH2:36][CH2:35][CH2:34][C:33]1=[O:38].C(N(CC)CC)C>ClCCl>[O:1]=[C:2]1[N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:5][CH:4]=[C:3]1[C:20]([O:22][C:37]1[CH2:36][CH2:35][CH2:34][C:33](=[O:38])[CH:32]=1)=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 130061,2-CyclohexanedioneHCID 1670692-Chloro-1-methylpyridinium iodideHCID 67954680HCID 67954680, compound2×

Product 1

HCID 67955046HCID 67955046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 7, Step C) (10.7 g, 36.3 mmol) in dichloromethane (150 mL) at ambient temperature was added 2-chloro-N-methylpyridinium iodide (also known as the Mukaiyama reagent) (14.8 g, 57.9 mmol) followed by cyclohexanedione (6.5 g, 58 mmol) and triethylamine (9.2 g, 91 mmol). The reaction mixture was left stirring at ambient temperature overnight, then diluted with dichloromethane, washed with water, brine and dried over anhydrous Na2SO4. The residue obtained after removal of the solvent under vacuum was purified by trituration with n-chlorobutane/petroleum ether mixtures to obtain 9.8 g of the title compound as a light brown solid.

Workup

  1. waitThe reaction mixture was left
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe residue obtained
  5. customafter removal of the solvent under vacuum
  6. customwas purified by trituration with n-chlorobutane/petroleum ether

Sources & evidence

ORD record
ord-0c079651bb374cf8b38a186f2ed7ed72
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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