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

HRID 336924

반응식

HRID 336924 반응식
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]([CH3:39])(=[O:38])=[O:37])=O.[F:40][C:41]([F:53])([F:52])[C:42]1[CH:43]=[C:44]([NH:48][C:49]([NH2:51])=[O:50])[CH:45]=[CH:46][CH:47]=1.[C:54]([O:60][CH2:61][CH:62]=[CH2:63])(=[O:59])[CH2:55][C:56]([CH3:58])=O>CC(OC)(C)C>[C:32]([C:31]1[CH:34]=[CH:35][C:28]([CH:26]2[C:55]([C:54]([O:60][CH2:61][CH:62]=[CH2:63])=[O:59])=[C:56]([CH3:58])[N:48]([C:44]3[CH:45]=[CH:46][CH:47]=[C:42]([C:41]([F:52])([F:53])[F:40])[CH:43]=3)[C:49](=[O:50])[NH:51]2)=[C:29]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:30]=1)#[N:33]

참가 물질

7

반응물 5

HCID 6535Triethyl PhosphateHCID 14812Phosphorus oxide (P4O10)HCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 581337504-Formyl-3-(methylsulfonyl)benzonitrile

생성물 1

HCID 42642358Allyl(rac)-4-[4-cyano-2-(methylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

The reaction was carried out under argon. Triethyl phosphate (22.98 g, 126 mmol) and diphosphorus pentoxide (11.94 g, 84.1 mmol) were stirred at 50° C. overnight. The mixture was then diluted with MTBE (450 ml), and 4-formyl-3-(methylsulfonyl)benzonitrile (22.00 g, 105 mmol; Example 4A), 1-[3-(trifluoromethyl)phenyl]urea (21.47 g, 105 mmol) and allyl acetoacetate (22.42 g, 158 mmol) were added. The mixture was stirred under reflux overnight. Since the reaction was incomplete, the reaction mixture was concentrated by distillative removal of 350 ml of MTBE. The mixture was then heated under reflux for a further 4 h. For work-up, the solvent was removed under reduced pressure, and the residue was suspended in diethyl ether and then filtered off with suction. The solid was washed with dist. water (350 ml) and then with diethyl ether (50 ml). This gave 34.74 g (64% of theory) of the title compound.

후처리

  1. additionwere added
  2. temperatureunder reflux overnight
  3. concentrationthe reaction mixture was concentrated by distillative removal of 350 ml of MTBE
  4. temperatureThe mixture was then heated
  5. temperatureunder reflux for a further 4 h
  6. customFor work-up, the solvent was removed under reduced pressure
  7. filtrationfiltered off with suction
  8. washThe solid was washed with dist

출처 및 근거

ORD 기록
ord-02871a5d176d4231957fb565b166b82b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889700B2

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