2-Butyn-1-ol → 4-(2,6-Difluorobenzyl)-6-(2-butynyloxy)pyrimidine

HRID 1759868

반응식

HRID 1759868 반응식
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:16]=1[CH2:15][C:13]1[CH:14]=[C:9]([O:7][CH2:3][C:4]#[C:5][CH3:6])[N:10]=[CH:11][N:12]=1

참가 물질

6

반응물 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 225997014-Chloro-6-(2,6-difluorobenzyl)pyrimidine

생성물 1

HCID 225998624-(2,6-Difluorobenzyl)-6-(2-butynyloxy)pyrimidine수율 105.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

In 2 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride (60% in oil), to which 0.6 ml of a tetrahydrofuran solution containing 0.07 g of 2-butyn-1-ol were slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, to which 0.6 ml of a tetrahydrofuran solution containing 0.2 g of 4-chloro-6-(2,6-difluorobenzyl)pyrimidine was slowly added dropwise at room temperature, followed by stirring for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.24 g of 4-(2,6-difluorobenzyl)-6-(2-butynyloxy)pyrimidine (the present compound (80)), m.p.: 57.6° C.

후처리

  1. additionwere slowly added dropwise
  2. additionwas slowly added dropwise at room temperature
  3. stirringby stirring for 4 hours
  4. extractionextracted three times with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-28a589fbd71c42c296e5c2eab10f7e3c
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06838463B2

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