N,N-Dimethylaniline → HCID 57839032, compound

HRID 732958Notes

Reaction equation

HRID 732958 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:12][C:13](=O)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].O=P(Cl)(Cl)[Cl:29].CN(C)C1C=CC=CC=1>>[Cl:29][C:13]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:10]=[C:11]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:12]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 136093747HCID 136093747, compound

Product 1

HCID 57839032HCID 57839032, compoundYield 97%

Procedure

To a stirred solution of ethyl 4-(2,4-dichlorophenyl)-6-oxo-2-phenyl-1,6-dihydropyrimidine-5-carboxylate (372 mg, 0.91 mmol) in doixane (6 mL) was added POCl3 (0.4 mL, 4.55 mmol) and N,N-dimethylaniline (11.5 μL, 0.09 mmol). After 4 hrs at 70° C., the reaction was concentrated under reduced pressure and diluted with EtOAc (100 mL). The organic layer was extracted with saturated NaHCO3 solution (2×60 mL), brine (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The crude reaction product was purified by flash chromatography (silica gel, 30% EtOAc/hexane) to give ethyl 4-chloro-6-(2,4-dichlorophenyl)-2-phenylpyrimidine-5-carboxylate (360 mg, 97% for 3 steps) as a clear oil.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc (100 mL)
  3. extractionThe organic layer was extracted with saturated NaHCO3 solution (2×60 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude reaction product
  8. customwas purified by flash chromatography (silica gel, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-357f570f450449b6be5747e3f513c498
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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