Toluene → 5-Chloropyrido[3,4-b]pyrazin-2(1H)-one

HRID 627610

Reaction equation

[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[C:10](OCC)(=O)[CH:11]=[O:12].C1(C)C=CC=CC=1>C(O)C>[Cl:1][C:2]1[C:7]2[N:8]=[CH:10][C:11](=[O:12])[NH:9][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A suspension 2-chloropyridine-3,4-diamine (2.5 g, 17.41 mmol) and a 50% solution of ethyl glyoxalate in toluene (3.45 mL, 17.41 mmol) in ethanol (34.8 mL) was stirred at reflux for 24 hours. The solution was cooled to −20° C. for 16 hours, and the resulting precipitate was collected by vacuum filtration and rinsed with ethanol. The crude product was purified via reverse-phase HPLC, eluting with 5-50% acetonitrile/0.1% trifluoroacetic acid in water/0.1% trifluoroacetic acid, to afford the title compound (570 mg, 3.14 mmol). MS m/z=182 (M+H).

Workup

temperatureat reflux for 24 hours
filtrationthe resulting precipitate was collected by vacuum filtration
washrinsed with ethanol
customThe crude product was purified via reverse-phase HPLC
washeluting with 5-50% acetonitrile/0.1% trifluoroacetic acid in water/0.1% trifluoroacetic acid

Sources & evidence

ORD record: ord-e9ee707b04cb45c28ecff6ed49c8237b
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309263B2

Linked notes

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