Cyclohexyl isocyanate → 1-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

HRID 600396Notes

Reaction equation

HRID 600396 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[CH:25]1([N:31]=[C:32]=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>ClC(Cl)C>[CH:25]1([NH:31][C:32]([NH:1][C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:22])[CH3:24])[C:5]3=[N:6][CH:7]=2)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 578310481-[2-amino-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

Product 1

HCID 578310441-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureaYield 76%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 1-[2-amino-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.100 g, 0.287 mmol) and cyclohexyl isocyanate (0.37 mL, 2.9 mmol) in 3 mL of dichloroethane was stirred at reflux for 19 h, then concentrated to a residue. Column chromatography (10→50% EtOAc/hexanes) afforded 0.103 g (76%) of 1-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as a brown solid.

Workup

  1. temperatureat reflux for 19 h
  2. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-9ab0ee98522a41f480d40d495ebf3226
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

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