Diethyl Oxalate → 1-(2,4-difluorophenyl)-7-ethyl-1H-pyrazolo[3,4-b]pyrazine-5,6(4H,7H)-dione

HRID 383570Notes

Reaction equation

[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:23]([NH:24][CH2:25][CH3:26])=[C:22]([NH2:27])[CH:21]=[N:20]1>CCOC(C)=O>[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:23]2[N:24]([CH2:25][CH3:26])[C:2](=[O:4])[C:1](=[O:8])[NH:27][C:22]=2[CH:21]=[N:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of diethyl oxalate (5.68 mL, 4.20 mmol) and 1-(2,4-difluorophenyl)-N5-ethyl-1H-pyrazole-4,5-diamine (1.00 g, 4.20 mmol) were heated in an oil bath at 150° C. for 18 h. The reaction mixture was cooled to RT and treated with EtOAc (5 mL) and hexanes (15 mL). The precipitated tan solid was filtered and rinsed with 5 mL of ether to afford 1-(2,4-difluorophenyl)-7-ethyl-1H-pyrazolo[3,4-b]pyrazine-5,6(4H,7H)-dione. MS (ES+): 293.1 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to RT
filtrationThe precipitated tan solid was filtered
washrinsed with 5 mL of ether

Sources & evidence

ORD record: ord-76317cddd4554ad89872fed3bc723c7f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367671B2

Reaction notes

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