Benzyl Alcohol → 4-(Benzyloxy)-2-chloro-5-nitropyrimidine

HRID 2277291노트

반응식

HRID 2277291 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1.O>CN(C=O)C>[CH2:1]([O:8][C:14]1[C:15]([N+:19]([O-:21])=[O:20])=[CH:16][N:17]=[C:12]([Cl:11])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 5212662,4-Dichloro-5-nitropyrimidine

생성물 1

HCID 867313744-(Benzyloxy)-2-chloro-5-nitropyrimidine수율 4.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Benzyl alcohol (5.57 g) was added to a suspension of sodium hydride (oil, 60%, 2.06 g) in DMF (100 mL) by small portions at 0° C., and the obtained mixture was stirred at 0° C. for 30 min. The reaction mixture was cooled to 0° C., 2,4-dichloro-5-nitropyrimidine (10.0 g) was added thereto, and the obtained mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (670 mg). 1H NMR (300 MHz, DMSO-d6) δ 5.62 (2H, s), 7.24-7.73 (5H, m), 9.28 (1H, s).

후처리

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe obtained mixture was stirred at 0° C. for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layer were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-4f58860f7f94438b9cf503d061802f47
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133129B2

반응 노트

불러오는 중…