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

반응식

HRID 336954 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]([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]

참가 물질

7

반응물 5

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

생성물 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

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-93fb55141b164c87a44395773e928ac2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889700B2

연결된 노트

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