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

HRID 906005Notes

Reaction equation

HRID 906005 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[C:14]([NH2:16])[N:15]=[C:10]2[CH:9]=[CH:8]1.[CH:19]1([N:25]=[C:26]=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1(C)C=CC=CC=1>[CH:19]1([NH:25][C:26]([NH:16][C:14]2[N:15]=[C:10]3[CH:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:18])([CH3:17])[CH3:1])[C:11]3=[N:12][CH:13]=2)=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 593633695-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine

Product 1

HCID 673858151-cyclohexyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureaYield 137.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(2-Trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (1.32 g, 4.99 mmol) was dissolved in toluene (50 mL). Cyclohexylisocyanate (6.4 mL, 49.9 mmol) was added and the reaction mixture was heated to reflux for 88 hr, cooled to RT, and concentrated, and purified by SiO2 chromatography (150 g SiO2, DCM/MeOH 0 to 5% MeOH) to give 2.67 g of impure 1-cyclohexyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as a yellow solid (31% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 88 hr
  3. concentrationconcentrated
  4. custompurified by SiO2 chromatography (150 g SiO2, DCM/MeOH 0 to 5% MeOH)

Sources & evidence

ORD record
ord-817fc5b9e9d042859091b0eb4a25054a
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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