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

HRID 1617183Notes

Reaction equation

HRID 1617183 reaction equation
[OH-:1].[K+].[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][OH:14])[C:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]#N)=[CH:22][C:21]=2[F:29])=[C:6]([CH3:30])[N:5]=1.C[OH:32]>>[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][OH:14])[C:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:32])=[O:1])=[CH:22][C:21]=2[F:29])=[C:6]([CH3:30])[N:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68954091(S)-2-(4-((2-Amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

Product 1

HCID 68956559(S)-2-(4-((2-Amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetic acid

Conditions

Temperature
70 °C

Procedure

A 5M aqueous solution of potassium hydroxide (0.58 mL) was added to a stirred solution of the product from step (iv) (0.11 g) in MeOH (1.5 mL). The mixture was heated at 70° C. for 15 h. The solvent was evaporated under reduced pressure and the aqueous residue was adjusted to pH ˜7 with concentrated HCl. The aqueous was extracted with EtOAc and the combined organic phase was dried, filtered and evaporated to the subtitle compound, 0.102 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 to the subtitle compound, 0.102 g

Sources & evidence

ORD record
ord-b20c91ec4c134d3893fc3df069e25c3f
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

Loading…