Ethyl benzoylacetate → 2-Amino-6-phenylpyrimidin-4-ol

HRID 1355702Notes

Reaction equation

[C:1]([CH2:9][C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)O.[NH2:19][C:20]([NH2:22])=[NH:21]>C(O)C>[NH2:21][C:20]1[NH:22][C:10](=[O:12])[CH:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Following the method of Jaeger (Liebigs. Ann. Chem. 1891, 262, 365), a mixture of 12.4 ml (72 mmol) ethyl benzoylacetate and 7.79 g (43.2 mmol) guanidine carbonate in 25 ml ethanol was heated at 80° C. for 4 h. The reaction mixture was then cooled to room temperature and the resulting crystals collected by filtration and washed sequentially with ice-cold water and ethanol to afford 7.2 g (53%) 2-amino-6-phenyl-3H-pyrimidin-4-one as a white crystalline solid. EI-MS m/e (%): 187 (M+, 100).

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationthe resulting crystals collected by filtration
washwashed sequentially with ice-cold water and ethanol

Sources & evidence

ORD record: ord-049016dc76934bf9a77fbb3f2fb36ece
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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