2-cyclopentyl-6-ethylpyrimidin-4(3H)-one → 4-Chloro-2-cyclopentyl-6-ethylpyrimidine

HRID 1508929노트

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HRID 1508929 반응식
O(Cl)[Cl:2].[P+5].[CH:5]1([C:10]2[NH:15][C:14](=O)[CH:13]=[C:12]([CH2:17][CH3:18])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1>[OH-].[Na+]>[Cl:2][C:14]1[CH:13]=[C:12]([CH2:17][CH3:18])[N:11]=[C:10]([CH:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)[N:15]=1

참가 물질

4

반응물 2

HCID 1360851072-cyclopentyl-6-ethylpyrimidin-4(3H)-oneHCID 178479711HCID 178479711, 화합물

생성물 1

HCID 609214014-Chloro-2-cyclopentyl-6-ethylpyrimidine수율 57%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
100 °C

실험 절차

Phosphorus(V) oxychloride (150 g, 99.0 mmol) was slowly added to 2-cyclopentyl-6-ethylpyrimidin-4(3H)-one (18.9 g, 98.3 mmol) at 0° C. Then, the reaction mixture was warmed to 100° C. for 3 h. After this time, the mixture was cooled, diluted with sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/dichloromethane) to afford the title compound (5.1 g, 57%) as yellow oil. MW=210.70. 1H NMR (CDCl3, 300 MHz) δ 7.01 (s, 1H), 3.36-3.20 (m, 1H), 2.74 (q, J=7.5 Hz, 2H), 2.14-1.99 (m, 2H), 1.98-1.76 (m, 4H), 1.75-1.63 (m, 2H), 1.29 (t, J=7.5 Hz, 3H); APCI MS m/z 211 [M+H]+.

후처리

  1. temperatureAfter this time, the mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, hexanes/dichloromethane)

출처 및 근거

ORD 기록
ord-252381d0f4b64e1d8bdcf79e55672179
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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