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

HRID 906008Notes

Reaction equation

HRID 906008 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([C:20]([CH3:22])=[CH2:21])=[CH:18][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([CH:20]([CH3:21])[CH3:22])=[CH:18][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 673856211-cyclohexyl-3-[7-isopropenyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Product 1

HCID 673852491-Cyclohexyl-3-[7-isopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of 1-cyclohexyl-3-[7-isopropenyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (70 mg, 0.163 mmol) and Pd/C (17 mg, 0.016 mmol) in MeOH (1.6 mL) was shaked under 50 psi of H2 atmosphere overnight, filtered through a pad of celite, and washed with MeOH. The filtrate was concentrated to give crude 1-Cyclohexyl-3-[7-isopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea, which was dissolved in a solution of HCl in AcOH (1M, 1.6 mL). The reaction mixture was heated at 50° C. in the sealed tube for 2 hr, concentrated to dryness, dissolved in 2 mL of MeOH:H2O:Et3N 8:1:1 and ethylenediamine (0.11 mL, 1.63 mmol) was added. The reaction mixture was stirred overnight, concentrated and purified by SiO2 chromatography (8 g SiO2, DCM/MeOH 0 to 10% MeOH) to give 9 mg of 1-cyclohexyl-3-(7-isopropyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as a pale yellow solid (18% yield).

Workup

  1. customwas shaked under 50 psi of H2 atmosphere overnight
  2. filtrationfiltered through a pad of celite
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b2a8bf11a07a47e796b56bcdf7e19c48
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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