N-bromobutanimide → HCID 57600276, compound

HRID 2368628Notes

Reaction equation

HRID 2368628 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]2[C:9](=[O:21])[C:10]3[NH:11][CH:12]=[N:13][C:14]=3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7]2=[N:6][N:5]=1.[Br:22]N1C(=O)CCC1=O>C1COCC1>[NH2:1][CH2:2][CH2:3][C:4]1[N:8]2[C:9](=[O:21])[C:10]3[NH:11][C:12]([Br:22])=[N:13][C:14]=3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7]2=[N:6][N:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57600155HCID 57600155, compound

Product 1

HCID 57600276HCID 57600276, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-(2-aminoethyl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (310 mg, 1.1 mmol) in THF (50 mL), was added N-Bromosuccinimide (0.29 g, 1.6 mol). The mixture was stirred at 70° C. for 1 hour. The reaction mixture was concentrated. The solid was filtered and washed with EtOAc to yield the desired product (300 mg, 76% yield). LCMS calculated for C13H19BrN7O (M+H): 368.1, 370.1. Found: 368.0, 370.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe solid was filtered
  3. washwashed with EtOAc

Sources & evidence

ORD record
ord-b3acd77ee60f4917b4f98eca7efc1639
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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