Potassium Iodide → 2-(8-Chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile

HRID 984812Notes

Reaction equation

HRID 984812 reaction equation
[Cl:1][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.[C:15]([C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br)#[N:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:11]([CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[C:15]#[N:16])[C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 106618-ChlorotheophyllineHCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 88509802-(8-Chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Chlorotheophylline (20 g, 93.19 mmol) was dissolved in 800 ml of DMF and 2-cyanobenzyl bromide (18.28 g, 93.19 mmol), potassium carbonate (12.88 g, 93.19 mmol), and potassium iodide (10 mg, 0.06 mmol) were added. The mixture was stirred at room temperature for 20 hours. The solvent was evaporated and the residue was suspended in 900 ml of water and 900 ml of EtOAc, and compound (1A) was collected by filtration of the suspension. The layers in the mother liquor were separated and the aqueous layer was extracted with 3×500 ml of EtOAc. The combined organic layers were washed with 1×500 ml of water, and the solvent was evaporated to give compound (1A) as white crystals. Combined yield: 28.6 g (93%). Mp. 222.5-223.7° C.

Workup

  1. customThe solvent was evaporated
  2. filtration900 ml of EtOAc, and compound (1A) was collected by filtration of the suspension
  3. customThe layers in the mother liquor were separated
  4. extractionthe aqueous layer was extracted with 3×500 ml of EtOAc
  5. washThe combined organic layers were washed with 1×500 ml of water
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c37d1046755e4e23af97b0d53608881c
Source dataset
uspto-grants-2005_03
Patent number
US06869947B2

Reaction notes

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