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Sodium Hydroxide → HCID 136224351, compound

HRID 1399744
Notes
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Reaction equation

HRID 1399744 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18]C)=[O:17])=[C:10]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:9]=1.[OH-].[Na+]>CO>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([OH:18])=[O:17])=[C:10]([C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)[N:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136353452HCID 136353452, compound

Product 1

HCID 136224351HCID 136224351, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared according to general method D from methyl 2-(2-(2-hydroxyphenyl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.083 g; 0.213 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 0.041 g (51%) 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-cd72cdadb4d8445fb18b4883be732b6d
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906906B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes