Sodium Hydroxide → HCID 50996262, compound

HRID 1399567Notes

Reaction equation

HRID 1399567 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[N:8]=[C:7]([CH3:9])[C:6]([CH:10]([CH2:15][CH2:16][CH3:17])[C:11]([O:13]C)=[O:12])=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1.[OH-].[Na+]>C1COCC1>[CH3:24][N:2]([CH3:1])[C:3]1[N:8]=[C:7]([CH3:9])[C:6]([CH:10]([CH2:15][CH2:16][CH3:17])[C:11]([OH:13])=[O:12])=[C:5]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66955592HCID 66955592, compound

Product 1

HCID 50996262HCID 50996262, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(2-(dimethylamino)-4-methyl-6-phenylpyrimidin-5-yl)pentanoate (100 mg; 0.305 mmol) in THF (1 mL) and 2N sodium hydroxide solution (1.5 mL; 3 mmol) was placed in a sealed tube and irradiated in a microwave oven at 100° C. for 1 h and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and diluted with water. 1N Hydrochloric acid was added dropwise until the product precipitated. The solid was filtered and dried under reduced pressure to give 66 mg (69%) of the title compound as a white solid. ESI/APCI(+): 314 (M+H).

Workup

  1. customirradiated in a microwave oven at 100° C. for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. addition1N Hydrochloric acid was added dropwise until the product
  5. customprecipitated
  6. filtrationThe solid was filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-f373173e1a894d7d94b8b46c62df2637
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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