1-Butanol → 2-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

HRID 1617249Notes

Reaction equation

HRID 1617249 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(CC#N)=C[C:15]=2[O:23][CH3:24])=[C:4]([CH3:25])[N:3]=1.[OH-:26].[K+].[CH2:28]([OH:32])[CH2:29][CH2:30][CH3:31]>>[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:30]([CH2:29][C:28]([OH:26])=[O:32])=[CH:31][C:15]=2[O:23][CH3:24])=[C:4]([CH3:25])[N:3]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 689572822-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Product 1

HCID 684141782-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

Conditions

Temperature
100 °C

Procedure

The product from step (v) (2.1 g) was dissolved in butan-1-ol (20 mL) and aq. 5M KOH (3.71 ml) was added and the mixture was heated at 100° C. for 36 h. The mixture was allowed to cool and the solvent was evaporated under reduced pressure. The residue was diluted with water (5 mL) and the pH adjusted to ˜7 using cone HC. The resulting precipitate was collected by filtration and the solid was then suspended in MeCN (10 mL) for 10 min. The suspension was filtered and the solid dried under vacuum overnight to give the subtitle compound as as a white solid, 2.60 g.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with water (5 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. filtrationThe suspension was filtered
  6. customthe solid dried under vacuum overnight

Sources & evidence

ORD record
ord-7ba983ee61d84379894d772f0484e524
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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