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

HRID 1653709노트

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HRID 1653709 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-779d7402c00047fbbd1bfdc060a9d642
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05403845

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