Acetic Acid → HCID 59363389, compound

HRID 906030Notes

Reaction equation

HRID 906030 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]3[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]3=[N:16][CH:17]=2)=[O:10])[CH2:3]1.C(O)(=O)C>Cl.O.[OH-].[Na+]>[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]3[CH:20]=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[O:10])[CH2:3]1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 67386152HCID 67386152, compound

Product 1

HCID 59363389HCID 59363389, compoundYield 35.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

1-(3,3-Dimethyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.095 g, 0.227 mmol) was dissolved in 1M HCl in acetic acid (2 mL, 2.04 mmol) and the resulting yellow solution stirred at 50° C. for 1.5 hours. The reaction mixture was diluted with 2 mL of H2O and basified with 3M NaOH. Light yellow precipitate forms. The solvent was evaporated. The yellow solid was taken up in MeOH:H2O:Et3N 8:1:1 and stirred at RT for 1 hour. The mixture was absorbed onto SiO2 and purified by SiO2 chromatography (12 g SiO2, DCM/magic (DCM:MeOH:NH4OH 60:10:1) 0-35% magic) to give 0.023 g of 1-(3,3-dimethyl-cyclohexyl)-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as an off-white solid (35% yield).

Workup

  1. customThe solvent was evaporated
  2. stirringstirred at RT for 1 hour
  3. customThe mixture was absorbed onto SiO2
  4. custompurified by SiO2 chromatography (12 g SiO2, DCM/magic (DCM:MeOH:NH4OH 60:10:1) 0-35% magic)

Sources & evidence

ORD record
ord-640953db01b84e51b34c06421744ad8a
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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