1,1'-Carbonyldiimidazole → 1-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidine-5,7(4H,6H)-dione

HRID 1896204Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH2:15][CH3:16])=[N:4][N:5]([CH2:10][CH2:11][O:12][CH2:13][CH3:14])[C:6]=1[C:7]([NH2:9])=[O:8].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>CN(C)C=O>[CH2:13]([O:12][CH2:11][CH2:10][N:5]1[C:6]2[C:7](=[O:8])[NH:9][C:17](=[O:18])[NH:1][C:2]=2[C:3]([CH2:15][CH3:16])=[N:4]1)[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide from step 2 (2.44 g, 10.8 mmol) in N,N-dimethylformamide (40 mL) was treated with carbonyldiimidazole (1.92 g, 11.9 mmol) and heated at 80° C. overnight. The mixture was concentrated in vacuuo and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane as the eluent to provide 1.04 g of the title compound. MS (ESI) m/z 253.

Workup

concentrationThe mixture was concentrated in vacuuo
customthe residue was purified by column chromatography on silica gel using
additiona mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record: ord-f415cfce77a54f879508131baf452c9c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518956B2

Reaction notes

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