Dimethylformamide → 4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy]-2-pyrimidinecarbonitrile

HRID 1647410

반응식

HRID 1647410 반응식
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH3:12][C:13]([C:16]1[C:21]([O:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])=[C:20]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:19]=[C:18]([CH:33]=[N:34]O)[N:17]=1)([CH3:15])[CH3:14].N1C=CC=NC=1>C(#N)C>[CH3:15][C:13]([C:16]1[C:21]([O:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])=[C:20]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:19]=[C:18]([C:33]#[N:34])[N:17]=1)([CH3:12])[CH3:14]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 9260PyrimidineHCID 65578Oxalyl chlorideHCID 1363784124,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidinecarboxaldehyde oxime

생성물 1

HCID 199229864,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy]-2-pyrimidinecarbonitrile수율 22%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
0 °C

실험 절차

Dimethylformamide (0.05 g, 0.6 mmoles) is cooled to 0° C. in 10 mL of acetonitrile under argon. Oxalyl chloride (0.1 g, 0.9 mmoles) is added and the reaction mixture is stirred at 0° C. for 10 minutes. 4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy] -2-pyrimidinecarboxaldehyde oxime (0.2 g, 0.6 moles) is dissolved in 10 mL of acetonitrile and cooled to 0° C. The vilsmier reagent prepared above is added to the pyrimidine solution at 0° C. After 3 hours at 0° C., the reaction is quenched by the addition of 10 mL of saturated sodium bicarbonate and extracted with ether (3×10 mL). The organic extract is washed with 50 mL of brine and dried over magnesium sulfate. Evaporation of the solvent gives a red oil which is purified by flash chromatography (silica, 10% ether/chloroform) to give 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy]-2-pyrimidinecarbonitrile (43 mg, 22% ) as an oil. H1 -NMR (CDCl3) δ 5.04 (s, 2H, O--CH2 --O), 3.95 (m, 2H), 3.62 (m, 2H), 3.41 (s, 3H, OCH3), 1.44 (s, 18H, C(CH3)3 ).

후처리

  1. temperaturecooled to 0° C
  2. customThe vilsmier reagent prepared
  3. waitAfter 3 hours at 0° C.
  4. customthe reaction is quenched by the addition of 10 mL of saturated sodium bicarbonate
  5. extractionextracted with ether (3×10 mL)
  6. extractionThe organic extract
  7. washis washed with 50 mL of brine
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation of the solvent
  10. customgives a red oil which
  11. customis purified by flash chromatography (silica, 10% ether/chloroform)

출처 및 근거

ORD 기록
ord-2ae1f7370d9f415483617d707e28ccb9
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05432181

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