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Phosphorus oxychloride → (+/-)-2,4-Dichloro-5-(1-chloroethyl)-pyrimidine

HRID 2216955
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HRID 2216955 반응식
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9](O)[CH3:10])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([Cl:14])[CH3:10])=[CH:4][N:3]=1
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참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 151416481-(2,4-Dichloropyrimidin-5-yl)ethan-1-ol

생성물 1

HCID 21908976(+/-)-2,4-Dichloro-5-(1-chloroethyl)-pyrimidine

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
0 °C

실험 절차

To a solution of (±)-1-(2,4-dichloro-pyrimidin-5-yl)-ethanol (1.27 g, 6.60 mmol) (from Example 1a supra) in phosphorus oxychloride (5.0 mL, 53.11 mmol) (Aldrich), at 0° C., was added diisopropylethyl-amine (2.60 mL, 14.78 mmol) (Aldrich). The reaction was stirred at 0° C. for 5 minutes, at ambient temperature for 15 minutes and then at 115° C. for 3 hours. The reaction was cooled to room temperature, diluted with toluene (10 mL) and the mixture was then poured into ice (15 g). After stirring for 10 minutes, the layers were separated and the aqueous extract was back washed with toluene. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash chromatography (Biotage, 40M, 10:90 to 15:85 ethyl acetate-hexanes gradient) gave (±)-2,4-dichloro-5-(1-chloroethyl)-pyrimidine as an oil. (Yield 1.233 g; 88.3%).

후처리

  1. waitat 115° C. for 3 hours
  2. temperatureThe reaction was cooled to room temperature
  3. stirringAfter stirring for 10 minutes
  4. customthe layers were separated
  5. extractionthe aqueous extract
  6. washwas back washed with toluene
  7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash chromatography (Biotage, 40M, 10:90 to 15:85 ethyl acetate-hexanes gradient)

출처 및 근거

ORD 기록
ord-3724ae8fd7244cd3a5a0bbe008eff68d
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07112676B2

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