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

HRID 336942

반응식

HRID 336942 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][CH3:37])=O.[F:38][C:39]([F:51])([F:50])[C:40]1[CH:41]=[C:42]([NH:46][C:47]([NH2:49])=[O:48])[CH:43]=[CH:44][CH:45]=1.[C:52]([O:58][CH2:59][CH:60]=[CH2:61])(=[O:57])[CH2:53][C:54]([CH3:56])=O>CC(OC)(C)C>[C:32]([C:31]1[CH:34]=[CH:35][C:28]([CH:26]2[C:53]([C:52]([O:58][CH2:59][CH:60]=[CH2:61])=[O:57])=[C:54]([CH3:56])[N:46]([C:42]3[CH:43]=[CH:44][CH:45]=[C:40]([C:39]([F:50])([F:51])[F:38])[CH:41]=3)[C:47](=[O:48])[NH:49]2)=[C:29]([S:36][CH3:37])[CH:30]=1)#[N:33]

참가 물질

7

반응물 5

HCID 6535Triethyl PhosphateHCID 14812Phosphorus oxide (P4O10)HCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 581337424-Formyl-3-(methylsulfanyl)benzonitrile

생성물 1

HCID 44133410Allyl(rac)-4-[4-cyano-2-(methylsulfanyl)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 (1.46 g, 8.04 mmol) and diphosphorus pentoxide (761 mg, 5.36 mmol) were stirred at 50° C. overnight. The mixture was then diluted with MTBE (27 ml), and 4-formyl-3-(methylsulfanyl)benzonitrile (1.18 g, 6.70 mmol; Example 9A), 1-[3-(trifluoromethyl)phenyl]urea (1.37 g, 6.70 mmol) and allyl acetoacetate (1.43 g, 10.1 mmol) were added. The mixture was stirred under reflux overnight. For work-up, the solvent was removed under reduced pressure and the residue was suspended in diethyl ether and then filtered of with suction. This gave 978 mg (19% of theory) of the title compound.

후처리

  1. additionwere added
  2. temperatureunder reflux overnight
  3. customFor work-up, the solvent was removed under reduced pressure
  4. filtrationfiltered of with suction

출처 및 근거

ORD 기록
ord-95fe4ec652974181a0ac0a2ca4320375
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889700B2

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