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

HRID 336961Notes

Reaction equation

HRID 336961 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]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=O.[F:42][C:43]([F:55])([F:54])[C:44]1[CH:45]=[C:46]([NH:50][C:51]([NH2:53])=[O:52])[CH:47]=[CH:48][CH:49]=1.[C:56]([O:62][CH2:63][CH:64]=[CH2:65])(=[O:61])[CH2:57][C:58]([CH3:60])=O>CC(OC)(C)C>[C:32]([C:31]1[CH:34]=[CH:35][C:28]([CH:26]2[C:57]([C:56]([O:62][CH2:63][CH:64]=[CH2:65])=[O:61])=[C:58]([CH3:60])[N:50]([C:46]3[CH:47]=[CH:48][CH:49]=[C:44]([C:43]([F:54])([F:55])[F:42])[CH:45]=3)[C:51](=[O:52])[NH:53]2)=[C:29]([S:36]([CH:39]([CH3:41])[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 581338484-Formyl-3-[(1-methylethyl)sulfonyl]benzonitrile

Product 1

HCID 58133777Allyl (rac)-4-{4-cyano-2-[(1-methylethyl)sulfonyl]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 (1.049 g, 5.76 mmol) and diphosphorus pentoxide (0.454 g) were stirred at 40° C. overnight. The mixture was then diluted with MTBE (25 ml), and 4-formyl-3-[(1-methylethyl)sulfonyl]benzonitrile (0.759 g, 3.2 mmol), 1-[3-(tri-fluoromethyl)phenyl]urea (0.653 g, 3.2 mmol) and allyl acetoacetate (0.682 g, 4.8 mmol; 1.5 eq.) were added. The mixture was stirred under reflux for 6 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 (2×10 ml). This gave 1.25 g (48% of theory) of the title compound.

Workup

  1. additionwere added
  2. temperatureunder reflux for 6 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 (2×10 ml)

Sources & evidence

ORD record
ord-4fe3ec2edc72435584a961b47e28687d
Source dataset
uspto-grants-2014_11
Patent number
US08889700B2

Reaction notes

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