Sodium Hydroxide → HCID 86729289, compound

HRID 1399895Notes

Reaction equation

HRID 1399895 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([CH2:11][C:12]([O:14]CC)=[O:13])[C:6]=2[N:7]=1.[OH-].[Na+]>CCO.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([CH2:11][C:12]([OH:14])=[O:13])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86719804Ethyl 2-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate

Product 1

HCID 86729289HCID 86729289, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of ethyl 2-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate (1.25 g, 5.23 mmol) in EtOH/H2O (100 mL) was added NaOH (1.1 g, 26.15 mmol). The reaction mixture was stirred at room temperature until TLC showed completion. The reaction mixture was concentrated and the residue taken up in water (15 mL) and treated with 2M HCl until pH=3 then extracted with EA (2×25 ml). The combined organic layers were washed with brine (100 mL), dried over Na2SO4 and concentrated to yield the title product (600 mg, Yield 50%). The crude product was used in next step without further purification. LCMS (m/z): 212.0 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated with 2M HCl until pH=3
  3. extractionthen extracted with EA (2×25 ml)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f4a65b76118b4f3bb289dccd621b1f35
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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