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Potassium Carbonate → 7-isopropyl-5-[4-(2-nitrophenoxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 611526
Notes
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Reaction equation

HRID 611526 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:18]([CH3:20])[CH3:19])[C:4]=2[N:5]=[CH:6][N:7]=1.F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:18]([N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N+:28]([O-:30])=[O:29])=[CH:15][CH:16]=2)=[CH:9]1)([CH3:20])[CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 19597475HCID 19597475, compound

Product 1

HCID 195974577-isopropyl-5-[4-(2-nitrophenoxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-amino-5-(4-hydroxyphenyl)-7-isopropylpyrrolo[2,3-d]-pyrimidine (0.29 g), 2-fluoronitrobenzene (0.15 g), potassium carbonate (0.149 g) and N,N-dimethylformamide (4.0 ml) was shaken and heated at 120° C. for 5 hours. The mixture was evaporated to dryness under reduced pressure and the residue was partitioned between ethyl acetate (30 ml) and water (20 ml). The organic layer was separated, washed with water, and then with dilute sodium hydroxide solution, and then with brine, then dried, filtered and evaporated to give a solid which was triturated with ether to give 7-isopropyl-5-[4-(2-nitrophenoxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine. The structure was confirmed by 1H nmr.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (30 ml) and water (20 ml)
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialwith dilute sodium hydroxide solution, and then with brine, then dried
  6. filtrationfiltered
  7. customevaporated
  8. customto give a solid which
  9. customwas triturated with ether

Sources & evidence

ORD record
ord-73a0ae6ddff841c5803c86df9a19e173
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06001839

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes