Acetic Acid → 2-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

HRID 1617208Notes

Reaction equation

HRID 1617208 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17](CC#N)=[CH:16][CH:15]=2)=[C:4]([CH3:23])[N:3]=1.[C:24]([OH:27])(=[O:26])[CH3:25]>CO.[OH-].[K+].O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:25][C:24]([OH:27])=[O:26])=[CH:18][CH:19]=2)=[C:4]([CH3:23])[N:3]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 684144282-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile

Product 1

HCID 684164052-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

The product from step (v) in MeOH (10 ml) and 5M KOH in water (3 ml) was heated under reflux for 18 h. The mixture was neutralised with acetic acid then purified by RPHPLC to afford the subtitle compound, 0.168 g.

Workup

  1. temperatureunder reflux for 18 h
  2. customthen purified by RPHPLC

Sources & evidence

ORD record
ord-2741967b067548a3b9767a6ea83af5ca
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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