Ethyl isocyanate → 1-(6-Chloro-pyrido[2,3-b]pyrazin-3-yl)-3-ethyl-urea

HRID 1890503Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:12]=1)=[N:7][C:8]([NH2:11])=[CH:9][N:10]=2.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:12]=1)=[N:7][C:8]([NH:11][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[CH:9][N:10]=2

Participants

Conditions

Temperature: 100 °C

Procedure

A total of 5.0 g 6-Chloro-pyrido[2,3-b]pyrazin-3-ylamine (27.7 mmol; 1 eq) was suspended in 150 mL of dry 1,4-dioxane. 2.63 g (33.2 mmol; 1.2 eq) ethyl isocyanate was added and the reaction mixture was stirred at 100° C. for 4 hours. Additional 1.97 g (27.7 mmol; 1 eq) of ethyl isocyanate were added and the resulting solution was stirred at 100° C. for further 4 hours. After cooling to room temperature, the precipitate was filtered of and dried in vacuo to afford 6.5 g (93.3% yield) of 1-(6-Chloro-pyrido[2,3-b]pyrazin-3-yl)-3-ethyl-urea.

Workup

stirringthe resulting solution was stirred at 100° C. for further 4 hours
temperatureAfter cooling to room temperature
filtrationthe precipitate was filtered of and
customdried in vacuo

Sources & evidence

ORD record: ord-9714fa637cc8427894e265f9133cf0de
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507486B2

Reaction notes

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