Sodium Hydroxide → HCID 66956044, compound

HRID 1399752Notes

Reaction equation

HRID 1399752 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11]C)=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[N:5]=[C:4]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=[O:10])=[C:6]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[N:5]=[C:4]([NH:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66955518HCID 66955518, compound

Product 1

HCID 66956044HCID 66956044, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared according to general method D from methyl 2-(4-methyl-2-(phenylamino)-6-p-tolylpyrimidin-5-yl)pentanoate (0.058 g; 0.149 mmol), sodium hydroxide 10N (0.10 mL; 1.00 mmol) in methanol (1 mL) at 60° C. for 18 h. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water and extracted with diethyl ether. The pH of the aqueous layer was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N until a precipitate was formed. The suspension was extracted twice with ethyl acetate and the combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give 0.035 g (62%) of the title compound.

Workup

  1. customThis compound was prepared
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with diethyl ether
  5. additionThe pH of the aqueous layer was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N until a precipitate
  6. customwas formed
  7. extractionThe suspension was extracted twice with ethyl acetate
  8. dry with materialthe combined organic layers were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f8a8418107043d8b9cc6e56d53aa1b3
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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