Methanol → 2-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

HRID 2387811Notes

Reaction equation

HRID 2387811 reaction equation
[OH-:1].[K+].[NH2:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]#N)=[CH:14][C:13]=2[O:21][CH3:22])=[C:6]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:5]=1.C[OH:30]>>[NH2:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:30])=[O:1])=[CH:14][C:13]=2[O:21][CH3:22])=[C:6]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 689540842-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Product 1

HCID 689580582-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

Conditions

Temperature
65 °C

Procedure

A 5M aqueous solution of potassium hydroxide (5 mL) was added to a solution of the product from step (vii) (0.60 g) in MeOH (10 mL). The resulting mixture was stirred at 65° C. for 15 h. The mixture was allowed to cool and the solvent evaporated under reduced pressure. The resulting aqueous mixture was neutralised with 2M HCl and extracted with EtOAc. The combined organic phase was dried, filtered and evaporated to give the subtitle compound as a colourless solid 0.329 g that was used without further purification.

Workup

  1. temperatureto cool
  2. customthe solvent evaporated under reduced pressure
  3. extractionextracted with EtOAc
  4. customThe combined organic phase was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-894a57dcf1204a8cb4eaeabcd05224c5
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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