HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → 2-(4-Methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoic acid

HRID 1399585
Notes
Print preview

Reaction equation

HRID 1399585 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]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:3]=1.[OH-].[Na+]>O1CCCC1>[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]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50994994Methyl 2-(4-methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 509976972-(4-Methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoic acidYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-(4-methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoate (80 mg; 0.214 mmol) in tetrahydrofuran (2.136 mL) was added a 10 N sodium hydroxide solution (214 μL; 2.136 mmol) and the mixture was heated at 100° C. for 18 h. The volatiles were removed under reduced pressure and the mixture was acidified by adding 6N hydrochloric acid. The suspension was extracted twice with ethyl acetate. The combined organic layers were washed with a saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure to give 31 mg (40%) of the title compound as a white solid. ESI/APCI(+): 361 (M+H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionby adding 6N hydrochloric acid
  3. extractionThe suspension was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47fc2dc2311c4d218d3079fd49f6078c
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906906B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes