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

HRID 227707ノート

反応式

HRID 227707 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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]+

後処理

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

出典と根拠

ORDレコード
ord-fa72a0ad3f224cd894286aa0c4c2f465
出典データセット
uspto-grants-2009_07
特許番号
US07560467B2

反応ノート

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