Sodium hydride → HCID 20207338, compound

HRID 464350Notes

Reaction equation

HRID 464350 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[H][H].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[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][CH:11]=[CH:10][N:9]=1)[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 10606924N-(3-aminopropyl)pyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 20207338HCID 20207338, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of sodium hydride (0.95 g) and 2-(3-aminopropylamino) pyridine (5.4 g) in DMSO (25 ml) was heated slowly to 85° C. under nitrogen. After the evolution of hydrogen had ceased the solution was cooled to room temperature and 4-methoxybenzyl chloride (5.59 g) in DMSO (5 ml) added dropwise keeping the temperature below 30° C. After a further 1 hr, water (300 ml) was added and the mixture extracted with ether. The extract was washed with 2N hydrochloric acid. The pH of the acid washings was adjusted to 4-5. After extracting with chloroform the pH was raised to 14 and extracted with ether. The ether extract was washed with water, dried (K2CO3) and stripped to give 2-[N-(3-aminopropyl)-N-(4-methoxybenzyl)-amino]pyridine (7.19 g) as an oil which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-(4-methoxybenzyl)amino]pyridine (1.0 g) and 2-nitroamino-5-(6-methylpyrid-3 -ylmethyl)pyrimid-4-one (0.8 g) were heated together under reflux in pyridine (10 ml) for 20 hr. On cooling, the mixture was stripped, the residue triturated with ether and recrystallised twice from ethanol/water to give 2-[3-[N-(4-methoxybenzyl)-N-pyrid-2-ylamino]propylamino]-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one 1H2O, 0.72 g (48%), mp 90°-98° C. (softens).

Workup

  1. temperaturewas cooled to room temperature
  2. customthe temperature below 30° C
  3. extractionthe mixture extracted with ether
  4. washThe extract was washed with 2N hydrochloric acid
  5. extractionAfter extracting with chloroform the pH
  6. temperaturewas raised to 14
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. washwas washed with water
  10. dry with materialdried (K2CO3)

Sources & evidence

ORD record
ord-171ab80cd99c40b38fff84f4de7a4609
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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