Ethylene carbonate → HCID 19597460, compound

HRID 611538Notes

Reaction equation

HRID 611538 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:21]([NH2:23])=[N:20][CH:19]=[N:18][C:17]=3[NH:16][CH:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(=O)O[CH2:27][CH2:26][O:25]1.[OH-].[Na+]>CN(C)C=O>[NH2:23][C:21]1[C:22]2[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:12]=3)=[CH:15][N:16]([CH2:27][CH2:26][OH:25])[C:17]=2[N:18]=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 14798Sodium HydroxideHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 19597460HCID 19597460, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (0.50 g), ethylene carbonate (0.16 g), N,N-dimethylformamide (20 ml) and a catalytic amount of sodium hydroxide powder was boiled under reflux for 1 hour. The mixture was evaporated under reduced pressure and the residue was triturated with water (30 ml). The mixture was filtered to give a solid which was purified by flash column chromatography on silica using ethyl acetate/industrial methylated spirit (9:1) as the mobile phase to give 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]ethanol, m.p. 144.5-145° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe mixture was evaporated under reduced pressure
  3. customthe residue was triturated with water (30 ml)
  4. filtrationThe mixture was filtered
  5. customto give a solid which
  6. customwas purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-f0aa3248bc35407d98cf89bd54cefde8
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

Loading…