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

HRID 1617166Notes

Reaction equation

HRID 1617166 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[F:21])=[C:6]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:5]=1.C[OH:29]>>[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:29])=[O:1])=[CH:14][C:13]=2[F:21])=[C:6]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 684148972-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

Product 1

HCID 689594772-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorophenyl)acetic acid

Conditions

Temperature
65 °C

Procedure

A 5M aqueous solution of potassium hydroxide (3.10 mL) was added to a solution of the product of step (vii) (0.53 g) in MeOH (6 mL). The mixture was stirred at 65° C. for 15 h and allowed to cool. The solvent was evaporated under reduced pressure and the resulting aqueous solution adjusted to pH ˜7 with conc. HCl. The aqueous phase was extracted with DCM and EtOAc, the combined organic phase was evaporated under reduced pressure to give the subtitle compound as a colourless solid 0.547 g.

Workup

  1. temperatureto cool
  2. customThe solvent was evaporated under reduced pressure
  3. extractionThe aqueous phase was extracted with DCM and EtOAc
  4. customthe combined organic phase was evaporated under reduced pressure

Sources & evidence

ORD record
ord-36e98fd8e03440db8b10e39459de2b2c
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

Loading…