Hydrochloric Acid → HCID 59540829, compound

HRID 1677363Notes

Reaction equation

HRID 1677363 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[N:13]=2)[N:8]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:7]=1[CH3:35])=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[CH3:35][C:7]1[N:8]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[C:9]2=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[N:13]=[C:14]2[C:6]=1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59540559HCID 59540559, compound

Product 1

HCID 59540829HCID 59540829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ethyl ester (110 mg, 0.22 mmol) in 1.0 mL of THF was added a 500 uL of 5.0 M aqueous NaOH. Heated to 60° C. for 3 days. Diluted with THF, made acidic with 1.0 M HCl and partitioned into methylene chloride. Dried the organic phase over Na2SO4, filtered, and concentrated. Collect 107 mg of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid sufficiently pure for the next step.

Workup

  1. custompartitioned into methylene chloride
  2. dry with materialDried the organic phase over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customCollect 107 mg of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid sufficiently pure for the next step

Sources & evidence

ORD record
ord-07fc352071ce478aa98eee323e962964
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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