Urea → Methyl 4-(4-fluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 227707노트

반응식

HRID 227707 반응식
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[NH2:20][C:21]([NH2:23])=[O:22].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C1(C)C=CC=CC=1.O>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:3][O:2][CH3:1])[NH:23][C:21](=[O:22])[NH:20]2)=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 123500Methyl 4-methoxyacetoacetateHCID 2733225Ytterbium triflate

생성물 1

HCID 53439029Methyl 4-(4-fluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

Methyl 4-(methyloxy)-3-oxobutanoate (2.0 g, 13.69 mmol, 1 equiv), 4-Fluorobenzaldehyde (1.7 g, 13.69 mmol, 1 equiv), urea (1.64 g, 27.34 mmol, 2 equiv), and ytterbium triflate (854 mg, 1.37 mmol, 0.1 equiv) were combined in Toluene (3 mL) and heated to 100° C. in a sealed tube for three hours. The residue was diluted with 10 mL of water and extracted with EtOAc (10 mL). The organic layer was washed with brine and concentrated en vacuo to yield 4.03 g of the title compound as a light yellow oil (100%). MS (ES+) m/e 295 [M+H]+

후처리

  1. extractionextracted with EtOAc (10 mL)
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated en vacuo

출처 및 근거

ORD 기록
ord-fa72a0ad3f224cd894286aa0c4c2f465
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560467B2

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