2-Benzylamino-4-(t-butylamino)-5-fluoropyrimidine → 2-Amino-4-(t-butylamino)-5-fluoropyrimidine

HRID 368428Notes

Reaction equation

HRID 368428 reaction equation
C([NH:8][C:9]1[N:14]=[C:13]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:12]([F:20])=[CH:11][N:10]=1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[NH2:8][C:9]1[N:14]=[C:13]([NH:15][C:16]([CH3:18])([CH3:17])[CH3:19])[C:12]([F:20])=[CH:11][N:10]=1

Participants

4

Reactant 1

HCID 221212622-Benzylamino-4-(t-butylamino)-5-fluoropyrimidine

Product 1

HCID 221212902-Amino-4-(t-butylamino)-5-fluoropyrimidineYield 53.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 8 ml of acetic acid were added 1.00 g of 2-benzylamino-4-(t-butylamino)-5-fluoropyrimidine together with 215 mg of 10% palladium on carbon, and the mixture was hydrogenated at 60° C. for ten days. The catalyst was separated by filtration, and the solvent and the like were distilled off under reduced pressure. The procedure of adding 10 ml of ethanol and concentrating under reduced pressure was repeated three times, and the residue was separated by column chromatography (silica gel, 25 g; eluent: chloroform, and then, chloroform:methanol, 200:1), and the corresponding fractions were collected and concentrated under reduced pressure to obtain 360 mg of the title compound as a pale gray solid.

Workup

  1. waitthe mixture was hydrogenated at 60° C. for ten days
  2. customThe catalyst was separated by filtration
  3. distillationthe solvent and the like were distilled off under reduced pressure
  4. additionThe procedure of adding 10 ml of ethanol
  5. concentrationconcentrating under reduced pressure
  6. customthe residue was separated by column chromatography (silica gel, 25 g
  7. customeluent: chloroform, and then, chloroform:methanol, 200:1), and the corresponding fractions were collected
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c70b95625d54b51b6e3c135d993c3e4
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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