Potassium Hydroxide → 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionic acid

HRID 51500Notes

Reaction equation

HRID 51500 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]([CH3:30])[C:25]([O:27]CC)=[O:26])[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[K+]>CO>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]([CH3:30])[C:25]([OH:27])=[O:26])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22736339ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate

Product 1

HCID 227363532-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionate (201 mg), aqueous potassium hydroxide solution (4 ml of 2M solution) and methanol (20 ml) was boiled under reflux for 1 hour. The mixture was concentrated under reduced pressure to around 5 ml and then diluted with water (30 ml). The mixture was hot filtered and filtrate was cooled and then acidified with dilute acetic acid until no further precipitation occurred. The mixture was heated on a hot plate until the gel which had been obtained became a finely divided solid. The solid was collected by filtration to give 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propionic acid, m.p. 239.5-241° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure to around 5 ml
  3. additiondiluted with water (30 ml)
  4. filtrationThe mixture was hot filtered
  5. temperaturefiltrate was cooled
  6. customacidified with dilute acetic acid until no further precipitation
  7. temperatureThe mixture was heated on a hot plate until the gel which
  8. customhad been obtained
  9. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-3e4ee56c3e2b413d9dc774cc6b0491a5
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

Loading…