Ethyl isocyanate → 1-(3-Chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea

HRID 1511817Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

100 mg of 3-chloropyrido[2,3-b]pyrazin-6-ylamine (0.55 mmol) were initially charged in 5 ml of pyridine and 44 μl of ethyl isocyanate (0.55 mmol) were added at room temperature. The mixture was left to stir at 75° C. for 3 h and then another 132 μl in total of ethyl isocyanate (1.65 mmol) were added to the reaction mixture is small portions over 18 h. The solvent was then removed under reduced pressure. The resulting solid was purified by means of column chromatography on silica gel (dichloromethane/methanol eluent). This gave a bright yellow solid.

Workup

waitThe mixture was left
customover 18 h
customThe solvent was then removed under reduced pressure
customThe resulting solid was purified by means of column chromatography on silica gel (dichloromethane/methanol eluent)
customThis gave a bright yellow solid

Sources & evidence

ORD record: ord-dd925f5d8d2b484b8ef5616e61be0e9d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217042B2

Reaction notes

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