Ethylenediamine → 1-(cis-2-methyl-cyclohexyl)-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea

HRID 905930Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([NH:11][C:12]1[N:13]=[C:14]2[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]2=[N:16][CH:17]=1)=[O:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N)CN>CN(C)C=O>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([NH:11][C:12]1[N:13]=[C:14]2[CH:20]=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1)=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(cis-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.3 g, 0.7 mmol), tetrabutyl ammonium fluoride (1 M in THF, 4.6 mL, 4.6 mmol) and ethylene diamine (0.46 mL, 4.2 mmol) in 5 mL of N,N-dimethylformamide was stirred at 80° C. for 20 h, then concentrated. The resulting residue was triturated in methanol, and solid was isolated by filtration, washing with ether, and dried to afford 0.060 g (30%) of 1-(cis-2-methyl-cyclohexyl)-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as an off-white solid.

Workup

concentrationconcentrated
customThe resulting residue was triturated in methanol
customsolid was isolated by filtration
washwashing with ether
customdried

Sources & evidence

ORD record: ord-aa7b4597554d4a3580659aa8c539e797
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012974B2

Reaction notes

Loading…