Sodium Iodide → HCID 12003975, compound

HRID 971240Notes

Reaction equation

HRID 971240 reaction equation
[I-].[Na+].I.[CH2:4]([N:11]1[CH2:20][CH2:19][C:18]2[C:17](Cl)=[N:16][CH:15]=[N:14][C:13]=2[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:22][C:23]1[CH:24]=[N:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2>O1CCOCC1>[CH2:4]([N:11]1[CH2:20][CH2:19][C:18]2[C:17]([NH:22][C:23]3[CH:24]=[N:25][C:26]4[C:31]([CH:32]=3)=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:16][CH:15]=[N:14][C:13]=2[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 113753-AminoquinolineHCID 24841Hydrogen iodideHCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 1

HCID 12003975HCID 12003975, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Sodium iodide (434 mg, 2.9 mmol) and hydriodic acid (0.4 mL, 47% aqueous solution) were added to a mixture of 7-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (500 mg, 1.93 mmol) and 3-aminoquinoline (418 mg, 2.9 mmol) in dioxane (4 mL) and the reaction solution was heated in a sealed tube via microwave at 150° C. for 20 min. The solvent was removed under reduced pressure. The residue was suspended in water, solid sodium carbonate was added to a pH>8, and the mixture was extracted with ethyl acetate. The organic layer was removed in vacuo and the residue was purified by column chromatography to yield the product as a beige solid (405 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionsolid sodium carbonate was added to a pH>8
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was removed in vacuo
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2accb4acc1d04fa6b28103a5f33ca84a
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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