Lithium hydroxide, monohydrate → HCID 86672083, compound

HRID 82158Notes

Reaction equation

HRID 82158 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[N:6]=[CH:7][C:8]2[C:13]([I:14])=[CH:12][N:11]([C:15]([CH3:21])([CH3:20])[C:16]([O:18]C)=[O:17])[C:9]=2[N:10]=1>C1COCC1.O>[Cl:4][C:5]1[N:6]=[CH:7][C:8]2[C:13]([I:14])=[CH:12][N:11]([C:15]([CH3:21])([CH3:20])[C:16]([OH:18])=[O:17])[C:9]=2[N:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86672082Methyl 2-(2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropanoate

Product 1

HCID 86672083HCID 86672083, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium hydroxide monohydrate (4.08 g, 97.5 mmol) was added to methyl 2-(2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropanoate (18.5 g, 48.7 mmol) (see Preparation 41) in THF (185 mL) and water (45 mL). The mixture was stirred at 60° C. for 3 hours then the reaction mixture volume was reduced to one third by evaporation in vacuo. The aqueous residue was acidified using aqueous HCl (2.0 M) then extracted with EtOAc (4×200 mL). The organic phase was evaporated in vacuo and the crude material was triturated with hexane (100 mL) to afford the title compound as a white solid in 90% yield, 16.0 g.

Workup

  1. customthe reaction mixture volume was reduced to one third by evaporation in vacuo
  2. extractionthen extracted with EtOAc (4×200 mL)
  3. customThe organic phase was evaporated in vacuo
  4. customthe crude material was triturated with hexane (100 mL)

Sources & evidence

ORD record
ord-dcb91a7ad4a34ede8a5514e08b59beec
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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