Triethylamine → HCID 67065645, compound

HRID 1846383Notes

Reaction equation

HRID 1846383 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:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5][CH:4]=[C:3]1[C:20]([OH:22])=[O:21].C(Cl)(=O)C(Cl)=O.[C:29]1(=O)[CH2:34][CH2:33][CH2:32][C:31](=[O:35])[CH2:30]1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl.CN(C)C=O>[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]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:5][CH:4]=[C:3]1[C:20]([O:22][C:29]1[CH2:34][CH2:33][CH2:32][C:31](=[O:35])[CH:30]=1)=[O:21]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 66693235HCID 66693235, compound

Product 1

HCID 67065645HCID 67065645, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. Step B product (B) or the product from Step B1) (1.40 g, 4.8 mmol) in dichloromethane (30 mL) was added oxalyl chloride (1.21 g, 9.61 mmol) at 0° C. followed by catalytic amount (2 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. Then the reaction mixture was concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL), 1,3-cyclohexanedione (646 mg, 5.76 mmol), followed by triethylamine (976 mg, 9.60 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 dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (1.1 g).

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. stirringthe reaction mixture was stirred at room temperature for 30 min
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-dd79739e3e744f28bc820d83936b5217
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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