N-3-Bromopropylphthalimide → HCID 20186606, compound

HRID 464342

Reaction equation

HRID 464342 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Br[CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32]>CS(C)=O.CCOCC.O>[C:3]1([N:9]([CH2:19][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 81130N-2-PyridylanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 20186606HCID 20186606, compoundYield 35.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of sodium hydride (0.78 g) in DMSO (20 ml) was added 2-(N-phenylamino)pyridine (5.0 g) in DMSO (15 ml). The mixture was stirred and slowly heated under nitrogen to 85° C. After the evolution of hydrogen had ceased the mixture was cooled to room temperature and N-(3-bromopropyl)phthalimide (7.88 g) in DMSO (15 ml) added dropwise. After standing overnight the mixture was poured into water and ether extracts made with the pH adjusted between 2 to 4. The extracts were dried (MgSO4), stripped and the residue crystallised from ethanol to give N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide, 3.69 g (35%) mp 103°-5° C. (ii) N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide (3.1 g) and conc. hydrochloric acid (30 ml) were heated under reflux for 21 hr. Phthalic acid was filtered off on cooling and the filtrate stripped. The residue was taken back up in water and the solution extracted at pH 1 with chloroform. The pH was raised to 13 (NaOH) and the solution extracted again with ether. The ether extracts were dried (K2CO3) and stripped to give 2-[N-(3-aminopropyl)-N-phenylamino]pyridine, 1.84 g as an oil. (iii) 2-[N-(3-aminopropyl)-N-phenylamino]pyridine (0.9 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (0.86 g) were heated together under reflux in pyridine (2.5 ml) for 24 hr. The mixture was stripped and the residue recrystallised from ethanol to give 2-[3-(N-phenyl-N-pyrid-2-ylamino) propylamino]-5-(6-methylpyrid-3-ylmethyl) pyrimid-4-one, 1.03 g (73%) mp 216°-18° C.

Workup

  1. temperaturewas cooled to room temperature
  2. dry with materialThe extracts were dried (MgSO4)
  3. customthe residue crystallised from ethanol

Sources & evidence

ORD record
ord-8f12a38712d14c30b972ba9717c69390
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Linked notes

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