Acetic Acid → HCID 89629949, compound

HRID 882115Notes

Reaction equation

HRID 882115 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:11]3[C:12]4[C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][N:17]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:13]=4[N:14]=[CH:15][N:16]=3)[CH:7]=[CH:8]2)=[N:3]1.[Li+].[OH-].CC(O)=O>CO>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:11]3[C:12]4[C:19]([C:20]([OH:22])=[O:21])=[CH:18][N:17]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:13]=4[N:14]=[CH:15][N:16]=3)[CH:7]=[CH:8]2)=[N:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 89629948HCID 89629948, compound

Product 1

HCID 89629949HCID 89629949, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 4-(2-methyl-2H-indazol-6-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate in MeOH (2.0 mL) was added 2 M aqueous LiOH (1.1 mL) and the reaction mixture was heated at 60° C. for 17 hours. The reaction mixture was then acidified with AcOH and extracted with EtOAc (×3). The combined organic layers were then washed with brine, dried with sodium sulfate, filtered and concentrated under reduced pressure to give 4-(2-methyl-2H-indazol-6-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid. No further purification was carried out. LRMS (ESI) calc'd for C21H26SiN5O3 [M+H]+: 424, found 424.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washThe combined organic layers were then washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8fbd37936bc4f3da70d18eae53fc037
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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