Hydrochloric Acid → 2-amino-5-fluoro-6-furan-2-yl-3H-pyrimidin-4-one

HRID 1355861노트

반응식

HRID 1355861 반응식
C([O:3][C:4](=O)[CH:5]([F:13])[C:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)=O)C.C(=O)(O)O.[NH2:19][C:20]([NH2:22])=[NH:21].Cl>C(O)C.O>[NH2:21][C:20]1[NH:22][C:4](=[O:3])[C:5]([F:13])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:19]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 286947Carbonic acid-guanidine (1:1)HCID 45080919Ethyl 2-fluoro-3-(furan-2-yl)-3-oxopropanoate

생성물 1

HCID 1357249952-amino-5-fluoro-6-furan-2-yl-3H-pyrimidin-4-one수율 72%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Following the method of Skulnick and Wierenga (Patent WO 86/04583), a mixture of 8.72 g (43.6 mmol) (RS)-2-fluoro-3-furan-2-yl-3-oxo-propionic acid ethyl ester and 8.89 g (49.3 mmol) guanidine carbonate in 30 ml ethanol was heated at 100° C. for 16 hours. The reaction mixture was then cooled to 0° C. and diluted with 100 ml water. 1M hydrochloric acid was added dropwise until the mixture was ca pH 3, whereupon the resulting crystals were collected by filtration and washed sequentially with water and with ether to afford 6.11 g (72%) 2-amino-5-fluoro-6-furan-2-yl-3H-pyrimidin-4-one as a brown crystalline solid. EI-MS m/e (%): 95 (M+, 100), 154 ([M—MeCN]+, 24).

후처리

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. filtrationwhereupon the resulting crystals were collected by filtration
  3. washwashed sequentially with water and with ether

출처 및 근거

ORD 기록
ord-211b3959d7364457bb7dfdc95f29578c
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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