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

HRID 1355861ノート

反応式

HRID 1355861 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-211b3959d7364457bb7dfdc95f29578c
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

反応ノート

読み込み中…