Tetrahydrofuran → 2-(N-ethoxymethylanilino)-4-methyl-6-(1-propynyl) pyrimidine

HRID 981484

반응식

HRID 981484 반응식
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:20]1[CH2:24]C[CH2:22][CH2:21]1>CS(C)=O>[CH2:21]([O:20][CH2:24][N:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:22]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86296Mepanipyrim

생성물 1

HCID 143275592-(N-ethoxymethylanilino)-4-methyl-6-(1-propynyl) pyrimidine수율 62%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
50 °C

실험 절차

A solution of 2-anilino-4-methyl-6-(1-propynyl)-pyrimidine (2.5 g) in dimethyl sulfoxide (2.5 ml) were added to a suspension in 50 ml of tetrahydrofuran of 0.5 g of sodium hydride (60%) of which oily component was removed, and the mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, 1.5 g of chloromethyl ethyl ether was added thereto and the resulting mixture was stirred for 5 hours. The reaction mixture was poured into water and extracted with 150 ml of toluene. The toluene layer was washed wit water, dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The rsidue was purified by silica gel column chromatography to obtain 1.6 g (yield: 62%) of 2-(N-ethoxymethylanilino)-4-methyl-6-(1-propynyl) pyrimidine.

후처리

  1. customwas removed
  2. temperatureAfter cooling to room temperature
  3. addition1.5 g of chloromethyl ethyl ether was added
  4. stirringthe resulting mixture was stirred for 5 hours
  5. additionThe reaction mixture was poured into water
  6. extractionextracted with 150 ml of toluene
  7. washThe toluene layer was washed wit water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customThe rsidue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-cf1ffae5a76a4e4ca0f2cd1d6f4ff506
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992438

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