Triethylamine → HCID 66693718, compound

HRID 714412Notes

Reaction equation

HRID 714412 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:5][CH:4]=[C:3]1[C:21]([OH:23])=[O:22].C(Cl)(=O)C(Cl)=O.O[C:31]1[N:35]([CH2:36][CH3:37])[N:34]=[CH:33][CH:32]=1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl.CN(C)C=O>[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:5][CH:4]=[C:3]1[C:21]([O:23][C:31]1[N:35]([CH2:36][CH3:37])[N:34]=[CH:33][CH:32]=1)=[O:22]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 67954838HCID 67954838, compound2×HCID 178418331HCID 178418331, compound

Product 1

HCID 66693718HCID 66693718, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 2, Step C) (1.20 g, 3.92 mmol) in dichloromethane (30 mL) was added oxalyl chloride (998 mg, 7.84 mmol) at 0° C. followed by a catalytic amount (4-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 (30 mL) and 5-hydroxy-1-ethyl-1H-pyrazole, (572 mg, 4.7 mmol), followed by triethylamine (1.18 g, 11.8 mmol), and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 70% ethyl acetate in hexanes to afford the title product as a white solid (700 mg).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. stirringthe reaction mixture was stirred at room temperature for 30 min
  3. extractionwas then 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 70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6190e2d0719546e4b50c17470bdd5d24
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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