Lithium Hydroxide → HCID 58368042, compound

HRID 1260307Notes

Reaction equation

HRID 1260307 reaction equation
C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:10][CH:9]=[C:8]([CH2:19][CH3:20])[N:7]=1)=[O:5])C.[OH-].[Li+]>C1COCC1.C(O)C>[CH2:19]([C:8]1[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:10][CH:9]=1)[CH3:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58368048HCID 58368048, compound

Product 1

HCID 58368042HCID 58368042, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
0 °C

Procedure

6-Ethyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester (prepared according to US 2006/199960; 200 mg, 0.73 mmol) was dissolved in a THF/ethanol (12 ml/3 ml) mixture, cooled to 0° C. and treated with lithium hydroxide (2.2 ml, 1N aqueous solution). The reaction mixture was allowed to warm-up to ambient temperature and stirring was continued at that temperature for 2 hours. The pH value was subsequently adjusted to acidic and the reaction mixture was extracted with dichloromethane (3×40 ml). The combined organic phases were dried and evaporated to yield the product as light yellow solid (175 mg, 97%).

Workup

  1. temperatureto warm-up to ambient temperature
  2. extractionwas extracted with dichloromethane (3×40 ml)
  3. customThe combined organic phases were dried
  4. customevaporated

Sources & evidence

ORD record
ord-ef04bd96133346e9afa96e45ea4d6039
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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