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

HRID 1355861Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-211b3959d7364457bb7dfdc95f29578c
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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