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

HRID 610202Notes

Reaction equation

HRID 610202 reaction equation
[C:1]([NH:5][C:6]1[C:11]([F:12])=[CH:10][N:9]=[C:8](Cl)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN1CCCC1=O>[CH2:14]([NH:21][C:8]1[N:7]=[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:11]([F:12])=[CH:10][N:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 221212264-(t-Butylamino)-2-chloro-5-fluoropyrimidine

Product 1

HCID 221212622-Benzylamino-4-(t-butylamino)-5-fluoropyrimidineYield 78.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To 5 ml of N-methylpyrrolidone were added 1.8 g of 4-(t-butylamino)-2-chloro-5-fluoropyrimidine and 4.0 g of benzylamine, and the mixture was stirred at 140° C. for 17 hours and separated by adding 300 ml of distilled water and 40 ml of chloroform. The chloroform layer was washed twice with 300 ml of distilled water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The precipitated pale yellow crystals were dispersed in diisopropylether and collected by filtration to obtain 1.9 g of the title compound.

Workup

  1. customseparated
  2. additionby adding 300 ml of distilled water and 40 ml of chloroform
  3. washThe chloroform layer was washed twice with 300 ml of distilled water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe precipitated pale yellow crystals were dispersed in diisopropylether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6ecd9b7dcbaa4a3ea4661a985373e0db
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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