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

HRID 2387860Notes

Reaction equation

HRID 2387860 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-498581b155d64a3a84786a120599723d
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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