Triethylamine → HCID 67955156, compound

HRID 714415Notes

Reaction equation

HRID 714415 reaction equation
[F:1][C:2]1[C:3]([CH3:24])=[C:4]([N:8]2[C:13](=[O:14])[C:12]([C:15]([OH:17])=[O:16])=[CH:11][N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[C:31]1(=O)[CH2:36][CH2:35][CH2:34][C:33](=[O:37])[CH2:32]1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl.CN(C)C=O>[F:1][C:2]1[C:3]([CH3:24])=[C:4]([N:8]2[C:13](=[O:14])[C:12]([C:15]([O:17][C:31]3[CH2:36][CH2:35][CH2:34][C:33](=[O:37])[CH:32]=3)=[O:16])=[CH:11][N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 67954591HCID 67954591, compound2×

Product 1

HCID 67955156HCID 67955156, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 5, Step B) (41.0 g, 126 mmol) in dichloromethane (400 mL) was added oxalyl chloride (31.05 g, 252.0 mmol) at 0° C. followed by a catalytic amount (7 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. The reaction mixture was then concentrated under reduced pressure. To the resulting residue was added dichloromethane (400 mL), 1,3-cyclohexanedione (17.03 g, 152 mmol), followed by triethylamine (38.30 g, 379 mmol) and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with dichloromethane. The organic layer was washed once with water. Then the organic layer was dried (MgSO4) and concentrated under reduced pressure. The resulting solid was washed with chlorobutane to afford the title product pure as an off-white solid (37.6 g).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. stirringthe reaction mixture was stirred at room temperature for 30 min
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed once with water
  5. dry with materialThen the organic layer was dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting solid was washed with chlorobutane

Sources & evidence

ORD record
ord-2a2cf45c522b47f5995b5666425e6a83
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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