Sodium Hydroxide → HCID 136599016, compound

HRID 1750319Notes

Reaction equation

HRID 1750319 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:8]([CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-:18].[Na+]>O1CCOCC1>[CH3:17][N:8]1[C:4]2[N:5]=[CH:6][NH:7][C:2](=[O:18])[C:3]=2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89810919HCID 89810919, compound

Product 1

HCID 136599016HCID 136599016, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 4-chloro-7-methyl-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine (1.32 g, 5.42 mmol) in 1,4-dioxane (40 ml) was added 2M sodium hydroxide (aq) solution (40 ml, 80 mmol). The solution was heated to 100° C. for 16 h. The solution was cooled and the organic solvent removed in vacuo. The aqueous mixture was extracted using ethyl acetate (3×40 ml) and the organic extract was discarded. The solid was collected and dried using a sintered funnel under vacuum to afford the title compound (0.86 g, 71%) which was used in the next step without further purification. LCMS RT=0.87 min, M+H+=226.1.

Workup

  1. temperatureThe solution was cooled
  2. customthe organic solvent removed in vacuo
  3. extractionThe aqueous mixture was extracted
  4. extractionthe organic extract
  5. customThe solid was collected
  6. customdried

Sources & evidence

ORD record
ord-6f4ab9d30811472580fb187450943735
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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