Water → 2-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine

HRID 1528676Notes

Reaction equation

HRID 1528676 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[NH:10][N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[C:22]1[N:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[C:24]([NH2:32])[N:23]=1.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:22]3[N:23]=[C:24]([NH2:32])[C:25]([N+:29]([O-:31])=[O:30])=[C:26]([NH2:28])[N:27]=3)[N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 59177864HCID 59177864, compoundHCID 1785059746-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 675169662-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

156 mg (about 66% pure, 0.636 mmol) of the compound from example 6A were dissolved in DMF (3.5 ml), 28 mg (0.70 mmol) of sodium hydride (60% in mineral oil) were then added and the mixture was stirred at RT for 2 h. 115 mg (0.604 mmol) of 2-chloro-5-nitropyrimidine-4,6-diamine (synthesis: Helvetica Chimica Acta (1951), 34, 835-40) were then added, and the reaction mixture was stirred at 80° C. for another 1 h. After cooling to RT, the mixture was added to water. The suspension obtained in this manner was filtered off and the solid was washed repeatedly with water and then dried under high vacuum. This gave 196 mg (77% of theory) of the title compound in solid form.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for another 1 h
  2. temperatureAfter cooling to RT
  3. customThe suspension obtained in this manner
  4. filtrationwas filtered off
  5. washthe solid was washed repeatedly with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-c92779079e9a4b4d81e7db4039c3d97e
Source dataset
uspto-grants-2015_07
Patent number
US09090609B2

Reaction notes

Loading…