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

HRID 981484

反応式

HRID 981484 の反応式
[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]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86296Mepanipyrim

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cf1ffae5a76a4e4ca0f2cd1d6f4ff506
出典データセット
uspto-grants-1991_02
特許番号
US04992438

関連ノート

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