Benzyl Bromide → HCID 20262870, compound

HRID 464364Notes

Reaction equation

HRID 464364 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.[H][H].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O.O>[NH2:3][CH2:4][CH2:5][CH2:6][N:7]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 107281442-N-(3-Aminopropyl)-amino-5-bromopyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 20262870HCID 20262870, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of sodium hydride (0.83 g) in DMSO (25 ml) was added 2-(3-aminopropylamino)-5-bromopyridine (4.6 g). The mixture was stirred and heated slowly, to 85° C. After the evolution of hydrogen had ceased the mixture was cooled to room temperature and benzyl bromide (3.42 g) in DMSO (5 ml) added dropwise maintaining the temperature below 30° C. After standing overnight, water was added and the mixture extracted with ether. The ether extract was washed with 2N hydrochloric acid. The pH of the acid extract was raised to 2.5 (NaOH) and extracted with chloroform. The pH was raised further to 14 and again extracted with chloroform. After drying (K2CO3), the final extract was stripped to give 2-[N-(3-aminopropyl)-N-benzylamino]-5-bromopyridine (4.6 g) as an oil which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-benzylamino]-5-bromopyridine (1.97 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (1.34 g) were heated together under reflux in pyridine (15 ml) for 20 hr. After stripping, the residue was triturated with ether, recrystallised from methanol and chromatographed (silica gel, 1-2% methanol/chloroform) to give 2-[3-[N-benzyl-N-(5-bromopyrid-2-yl)-amino]propylamino]-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one, 0.2H2O, 1.01 g (38%) mp 150°-55° C. (from ethanol).

Workup

  1. temperaturewas cooled to room temperature
  2. temperaturemaintaining the temperature below 30° C
  3. extractionthe mixture extracted with ether
  4. extractionThe ether extract
  5. washwas washed with 2N hydrochloric acid
  6. extractionThe pH of the acid extract
  7. temperaturewas raised to 2.5 (NaOH)
  8. extractionextracted with chloroform
  9. temperatureThe pH was raised further to 14
  10. extractionagain extracted with chloroform
  11. dry with materialAfter drying (K2CO3)
  12. extractionthe final extract

Sources & evidence

ORD record
ord-6a31d4e15b92427fbc8241018d456a76
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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