Cyclohexyl isocyanate → 1-cyclohexyl-3-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

HRID 905990Notes

Reaction equation

HRID 905990 reaction equation
[CH3:1][C:2]1[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[N:9]=[C:4]2[CH:3]=1.[CH:20]1([N:26]=[C:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>ClCCCl>[CH:20]1([NH:26][C:27]([NH:10][C:8]2[N:9]=[C:4]3[CH:3]=[C:2]([CH3:1])[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:18])([CH3:17])[CH3:19])[C:5]3=[N:6][CH:7]=2)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 673853776-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine

Product 1

HCID 673861051-cyclohexyl-3-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureaYield 95.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (58 mg, 0.208 mmol) was dissolved in 1,2-dichloroethane (2.1 mL). Cyclohexylisocyanate (0.54 mL, 4.16 mmol) was added and the reaction mixture was heated to reflux overnight, cooled to RT, concentrated, purified by SiO2 chromatography (12 g SiO2, hexanes/EtOAc 0-50% EtOAc) to give 80 mg of 1-cyclohexyl-3-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as a yellow solid (95% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. custompurified by SiO2 chromatography (12 g SiO2, hexanes/EtOAc 0-50% EtOAc)

Sources & evidence

ORD record
ord-b86041ec71cc4607b68051bed774e584
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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