Methanol → (S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

HRID 1617175Notes

Reaction equation

HRID 1617175 reaction equation
[OH-:1].[K+].[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])[C:7]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]#N)=[CH:20][C:19]=2[O:27][CH3:28])=[C:6]([CH3:29])[N:5]=1.C[OH:31]>>[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])[C:7]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:31])=[O:1])=[CH:20][C:19]=2[O:27][CH3:28])=[C:6]([CH3:29])[N:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68955240(S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Product 1

HCID 68953524(S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

Conditions

Temperature
70 °C

Procedure

A 5M aqueous solution of potassium hydroxide (0.5 mL) was added to stirred solution of the product from step (iv) (0.095 g) in MeOH (1 mL). The mixture was stirred at 70° C. for 15 h and then the solvent was evaporated under reduced pressure. The resulting aqueous solution was adjusted to pH ˜7 using concentrated HCl. The aqueous was extracted with EtOAc and the combined organic phase was dried, filtered and evaporated to give the subtitle compound, 0.09 g.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionThe aqueous was extracted with EtOAc
  3. customthe combined organic phase was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f92e1c9f8d8f42edb882b0036ba035b1
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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