2-Fluorobenzoic acid → 8-(2-Fluorophenyl)-7H-purine

HRID 1710732Notes

Reaction equation

HRID 1710732 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](O)=O.[OH-].[Na+]>O>[F:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]1[NH:8][C:7]2[C:2](=[N:3][CH:4]=[N:5][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 99352-Fluorobenzoic acidHCID 14798Sodium HydroxideHCID 837034,5-Diaminopyrimidine

Product 1

HCID 469416118-(2-Fluorophenyl)-7H-purineYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4,5-diaminopyrimidine (0.500 g), 2-fluorobenzoic acid (0.700 g) and polyphosphoric acid (25 mL) was heated at 180° C. for 3 hours. Then the reaction mixture was cooled and poured into water (500 mL). The solution was adjusted to pH=8-9 by addition of solid NaOH and the resulting precipitate was collected by filtration, washed with water and dried to give 8-(2-fluorophenyl)-purine (off-white powder, 88.5%).

Workup

  1. temperatureThen the reaction mixture was cooled
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-bca674850391435881cfcd98a1c73691
Source dataset
uspto-grants-2010_09
Patent number
US07790730B2

Reaction notes

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