Methanol → 2-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetic acid

HRID 1617192Notes

Reaction equation

HRID 1617192 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#N)=[CH:12][CH:11]=2)=[C:4]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:3]=1.[OH-:25].[K+].C[OH:28]>>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:28])=[O:25])=[CH:12][CH:11]=2)=[C:4]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 595906382-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetonitrile

Product 1

HCID 595906372-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetic acid

Procedure

A mixture of the product from step (vii) (1.2 g) and KOH (5M in water, 5 ml) in MeOH (15 ml) was heated under reflux for 18 h. The solvent was evaporated under reduced pressure and the residue dissolved in water (15 ml). The solution was adjusted to pH7 with 2M HCl then the solid filtered, washed with water then ether to afford the subtitle compound, 1.13 g LC-MS m/z 343 multimode+

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue dissolved in water (15 ml)
  5. filtrationthe solid filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-011277b018fc4c53892d7fd8fd081bba
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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