Ethyl Acetate → 3-Cyano-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester

HRID 222611Notes

Reaction equation

[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]=1.O/[C:10](/[C:16]([O-:18])=[O:17])=[C:11](/[OH:15])\[C:12]([O-:14])=O.[C:19](OCC)(=O)C>C(O)(=O)C>[CH3:19][O:18][C:16]([C:10]1[N:1]=[C:2]2[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]2[C:12](=[O:14])[C:11]=1[OH:15])=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

3-amino-4-pyrazole carbonitrile (400 mg, 3.7 mmol) and dihydroxyfumarate (978 mg, 5.5 mmol) were dissolved in glacial acetic acid (5 mL) and the mixture was heated to 100° C. After 2 d, the reaction was complete by HPLC analysis and was cooled to room temperature. Ethyl acetate (10 mL) was added to initiate precipitation of product and the resulting precipitate was collected by filtration. The product was isolated in 62% yield (534 mg).

Workup

temperaturewas cooled to room temperature
customprecipitation of product
filtrationthe resulting precipitate was collected by filtration
customThe product was isolated in 62% yield (534 mg)

Sources & evidence

ORD record: ord-0f8d9abf64a14fadac1e9bb860676ea3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207334B2

Reaction notes

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