Triethyl Phosphate → Allyl(rac)-4-[4-cyano-2-(ethylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 336954

Reaction equation

HRID 336954 reaction equation
P(OCC)(OCC)(OCC)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH:26]([C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[S:36]([CH2:39][CH3:40])(=[O:38])=[O:37])=O.[F:41][C:42]([F:54])([F:53])[C:43]1[CH:44]=[C:45]([NH:49][C:50]([NH2:52])=[O:51])[CH:46]=[CH:47][CH:48]=1.[C:55]([O:61][CH2:62][CH:63]=[CH2:64])(=[O:60])[CH2:56][C:57]([CH3:59])=O>CC(OC)(C)C>[C:32]([C:31]1[CH:34]=[CH:35][C:28]([CH:26]2[C:56]([C:55]([O:61][CH2:62][CH:63]=[CH2:64])=[O:60])=[C:57]([CH3:59])[N:49]([C:45]3[CH:46]=[CH:47][CH:48]=[C:43]([C:42]([F:53])([F:54])[F:41])[CH:44]=3)[C:50](=[O:51])[NH:52]2)=[C:29]([S:36]([CH2:39][CH3:40])(=[O:38])=[O:37])[CH:30]=1)#[N:33]

Participants

7

Reactant 5

HCID 6535Triethyl PhosphateHCID 14812Phosphorus oxide (P4O10)HCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 581338333-(Ethylsulfonyl)-4-formylbenzonitrile

Product 1

HCID 58133859Allyl(rac)-4-[4-cyano-2-(ethylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
90 °C

Procedure

The reaction was carried out under argon. Triethyl phosphate (0.718 g, 3.9 mmol) and diphosphorus pentoxide (0.511 g) were stirred at 40° C. overnight. The mixture was then diluted with MTBE (30 ml), and 4-formyl-3-(ethylsulfonyl)benzonitrile (0.88 g, 3.94 mmol), 1-[3-(trifluoromethyl)phenyl]urea (0.805 g, 3.94 mmol) and allyl acetoacetate (0.841 g, 5.91 mmol; 1.5 eq.) were added. The mixture was then stirred under reflux for 4 h. The reaction mixture was then concentrated by distillative removal of MTBE and subsequently heated at 90° C. for a further 2 h. For work-up, residual solvent was removed under reduced pressure, and the residue was suspended in MTBE (20 ml) and then filtered off with suction. The solid was washed with MTBE (10 ml). This gave 1.34 g (42% of theory) of the title compound.

Workup

  1. additionwere added
  2. temperatureunder reflux for 4 h
  3. concentrationThe reaction mixture was then concentrated by distillative removal of MTBE
  4. customFor work-up, residual solvent was removed under reduced pressure
  5. filtrationfiltered off with suction
  6. washThe solid was washed with MTBE (10 ml)

Sources & evidence

ORD record
ord-93fb55141b164c87a44395773e928ac2
Source dataset
uspto-grants-2014_11
Patent number
US08889700B2

Linked notes

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