Methanol → HCID 59540720, compound

HRID 1677412Notes

Reaction equation

HRID 1677412 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([C:13]3[N:14]=[C:15]4[C:21]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:20][N:19](COCC[Si](C)(C)C)[C:16]4=[N:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].CO.[Cl:40][CH2:41][Cl:42]>FC(F)(F)C(O)=O>[NH4+:6].[OH-:27].[Cl:40][CH2:41][Cl:42].[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([C:13]3[N:14]=[C:15]4[C:21]([C:22](=[O:27])[C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:20][NH:19][C:16]4=[N:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344Dichloromethane2×HCID 14797Potassium HydroxideHCID 67204389HCID 67204389, compound

Product 2

HCID 21919329HCID 21919329, compoundHCID 59540720HCID 59540720, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-[2-(3-Cyclopentylamino-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.1781 g, 0.361 mmol) in 1 mL of dichloromethane and 1 mL of trifluoroacetic acid was stirred for 3 h then concentrated to a yellow oil. The oil was dissolved in 1 mL of methanol and the solution was treated with potassium hydroxide (0.24 g, 4.34 mmol). Preparative thin layer chromatography (50% 60:10:1 CH2Cl2:MeOH:NH4OH/dichloromethane) afforded 0.070 g (53% yield) of 1-[2-(3-Cyclopentylamino-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow solid.

Workup

  1. concentrationthen concentrated to a yellow oil
  2. dissolutionThe oil was dissolved in 1 mL of methanol

Sources & evidence

ORD record
ord-65a87231be6e4dd8a5cb164b449667fb
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

Loading…