Ethanol → 1-Methyl-1,4,5,6-Tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

HRID 1653709ノート

反応式

HRID 1653709 の反応式
[H-].[Na+].[C:3](=[N:6][OH:7])([NH2:5])[CH3:4].[CH3:8][N:9]1[CH2:14][CH:13]([C:15](OC)=O)[CH2:12][N:11]=[CH:10]1.C(O)C>C1COCC1>[CH3:8][N:9]1[CH2:14][CH:13]([C:15]2[O:7][N:6]=[C:3]([CH3:4])[N:5]=2)[CH2:12][N:11]=[CH:10]1

参加物

6

反応物 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 152943851-Methyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

生成物 1

HCID 152943861-Methyl-1,4,5,6-Tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Sodium hydride (60% dispersion in mineral oil 112 mg, 2.8 mmol) and acetamidoxime (207 mg, 2.8 mmol) are suspended in dry THF (16 ml) in an oven dried round bottom flask under nitrogen with stirring at 0° C. After 10 minutes the grey suspension is refluxed for 30 minutes giving a white suspension. 1-Methyl-1,4,5,6-tetrahydro-5-methoxycarbonylpyrimidine (593 mg, 2.8 mmol) dissolved in dry THF (4 ml) and anhydrous ethanol (1 ml) is added via syringe and reflux continued 15 hours. The suspension is evaporated in vacuo to a yellow gum and chromatographed (silica, chloroform/methanol, 9:1) to yield 24 mg (rf=0.07, 4%) solids identified by 300 MHz nmr and ms m/z=180.

後処理

  1. customdried round bottom flask under nitrogen
  2. temperatureAfter 10 minutes the grey suspension is refluxed for 30 minutes
  3. customgiving a white suspension
  4. temperaturereflux
  5. customThe suspension is evaporated in vacuo to a yellow gum
  6. customchromatographed (silica, chloroform/methanol, 9:1)
  7. customto yield 24 mg (rf=0.07, 4%) solids

出典と根拠

ORDレコード
ord-779d7402c00047fbbd1bfdc060a9d642
出典データセット
uspto-grants-1995_04
特許番号
US05403845

反応ノート

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