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

HRID 2277291ノート

反応式

HRID 2277291 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 867313744-(Benzyloxy)-2-chloro-5-nitropyrimidine収率 4.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4f58860f7f94438b9cf503d061802f47
出典データセット
uspto-grants-2015_09
特許番号
US09133129B2

反応ノート

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