Hydrochloric Acid → HCID 90041030, compound

HRID 523025Notes

Reaction equation

HRID 523025 reaction equation
C(O[C:6]([N:8]1[C:12]2=[N:13][C:14]([Cl:18])=[C:15]([Br:17])[N:16]=[C:11]2[CH:10]=[CH:9]1)=[O:7])(C)(C)C.[CH2:19]=[O:20].[OH-].[Na+].Cl>O1CCOCC1.O>[Br:17][C:15]1[N:16]=[C:11]2[C:10]([CH2:19][OH:20])=[CH:9][N:8]([CH2:6][OH:7])[C:12]2=[N:13][C:14]=1[Cl:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 90041360HCID 90041360, compound

Product 1

HCID 90041030HCID 90041030, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-bromo-3-chloro-pyrrolo[2,3-b]pyrazine-5-carboxylic acid tert-butyl ester (6.0 g, 18.0 mmol) in 1,4-dioxane (100 mL) was added methanal (5.4 g, 180.4 mmol) and 1 M NaOH solution (54 mL) and the reaction mixture was stirred at room temperature for 16 h. 1.2 N HCl was added into the reaction mixture until the mixture reached pH 7. The reaction mixture was concentrated in vacuo and the residue obtained was diluted with water (50 mL) and extracted with ethyl acetate (150 mL×3). The organic layers were combined and concentrated in vacuo to give (2-bromo-3-chloro-7-hydroxymethyl-pyrrolo[2,3-b]pyrazin-5-yl)-methanol (4.4 g, 83%) as yellow solid. LC-MS: 292.2 (M−H). This was used directly without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. extractionextracted with ethyl acetate (150 mL×3)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23d217682cba41c6b4f0ef2e496fd494
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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