Carbonic acid-guanidine (1:1) → 2-amino-6-furan-2-yl-5-methyl-3H-pyrimidin-4-one

HRID 1356009

Reaction equation

C([O:3][C:4](=O)[CH:5]([CH3:13])[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]>C(O)C>[NH2:21][C:20]1[NH:22][C:4](=[O:3])[C:5]([CH3:13])=[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 Rorig and Nicholson (U.S. Pat. No. 2,710,867), a mixture of 3.00 g (15.3 mmol) (RS)-3-furan-2-yl-2-methyl-3-oxo-propionic acid ethyl ester and 1,38 g (7.65 mmol) guanidine carbonate in 20 ml ethanol was heated at 100° C. for 16 hours. The reaction mixture was then cooled to 0° C., whereupon the resulting crystals were collected by filtration and washed sequentially with water and with ice-cold ethanol to afford 1.80 g (62%) 2-amino-6-furan-2-yl-5-methyl-3H-pyrimidin-4-one as a white crystalline solid. ES-MS m/e (%): 190 ([M—H]−, 100).

Workup

temperatureThe reaction mixture was then cooled to 0° C., whereupon the resulting crystals
filtrationwere collected by filtration
washwashed sequentially with water and with ice-cold ethanol

Sources & evidence

ORD record: ord-e8151700ff21411b83c9c3d79e7486d6
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Linked notes

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