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

HRID 981479

반응식

HRID 981479 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]CC[CH2:21]1>>[CH3:21][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

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86296Mepanipyrim

생성물 1

HCID 143275582-(N-methoxymethylanilino)-4-methyl-6-(1-propynyl)pyrimidine수율 63%

실험 절차

2-Anilino-4-methyl-6-(1-propynyl)pyrimidine (2.2 g) was added to a suspension in 50 ml of tetrahydrofuran of 0.5 g of sodium hydride (60%) of which oily component was removed with n-hexane, and the mixture was stirred for 30 minutes at 50°-55° C. After cooling to room temperature, 1.0 g of chloromethyl methyl ether was added to the mixture and stirred for 3 hours. The reaction mixture was poured into water and extracted with 150 ml of toluene. the toluene layer was washed with water, dried over Glauber's salt and concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.7 g (yield: 63%) of 2-(N-methoxymethylanilino)-4-methyl-6-(1-propynyl)pyrimidine.

후처리

  1. customwas removed with n-hexane
  2. addition1.0 g of chloromethyl methyl ether was added to the mixture
  3. stirringstirred for 3 hours
  4. additionThe reaction mixture was poured into water
  5. extractionextracted with 150 ml of toluene
  6. washthe toluene layer was washed with water
  7. dry with materialdried over Glauber's salt
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a7caa4a59af64945bc3a477998e00b03
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992438

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