Ethanol → 2-(4-(2-Amino-4-(butylamino)-6-methylpyrimidin-5-ylthio)phenyl)acetic acid

HRID 1617258Notes

Reaction equation

HRID 1617258 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([S:13][C:14]2[CH:19]=[CH:18][C:17](CC#N)=[CH:16][CH:15]=2)=[C:4]([CH3:23])[N:3]=1.[OH-:24].[K+].[CH3:26][CH2:27][OH:28]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:26][C:27]([OH:24])=[O:28])=[CH:16][CH:15]=2)=[C:4]([CH3:23])[N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 684153862-(4-(2-Amino-4-(butylamino)-6-methylpyrimidin-5-ylthio)phenyl)acetonitrile

Product 1

HCID 684157402-(4-(2-Amino-4-(butylamino)-6-methylpyrimidin-5-ylthio)phenyl)acetic acid

Procedure

A mixture of the product from step (v) (610 mg) and aq. 5M KOH (2 ml) in EtOH (8 ml) was heated under reflux for 18 h. The mixture was purified by RPHPLC to give the subtitle compound as a solid, 392 mg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe mixture was purified by RPHPLC

Sources & evidence

ORD record
ord-3a047b80770649eca06d0cd12a12f313
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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