Triethylamine → HCID 67955046, compound

HRID 714422Notes

Reaction equation

HRID 714422 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-methyl pyridinium 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 tituration 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 tituration with n-chlorobutane/petroleum ether

Sources & evidence

ORD record
ord-045eccd2e0d445a78a130da594b249a0
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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