Hydrochloric Acid → 1,3-Dipropyl-8-(6-chloro-3-pyridyl)xanthine

HRID 14620Notes

Reaction equation

HRID 14620 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][N:3]=1.OC1C=CC(C(O)=O)=CN=1.[NH2:21][C:22]1[C:23](=[O:36])[N:24]([CH2:33][CH2:34][CH3:35])[C:25](=[O:32])[N:26]([CH2:29][CH2:30][CH3:31])[C:27]=1[NH2:28].Cl>C(Cl)Cl.N1C=CC=CC=1.[OH-].[Na+].O>[CH2:33]([N:24]1[C:23](=[O:36])[C:22]2[NH:21][C:6]([C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[N:28][C:27]=2[N:26]([CH2:29][CH2:30][CH3:31])[C:25]1=[O:32])[CH2:34][CH3:35]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 27821656-Chloronicotinoyl ChlorideHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 178418479HCID 178418479, compound

Product 1

HCID 100890701,3-Dipropyl-8-(6-chloro-3-pyridyl)xanthine

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

6-Chloronicotinoyl chloride, prepared from 6-hydroxynicotinic acid (1.44 g, 10.4 mmol), in CH2Cl2 (20 ml) was added dropwise to a solution of 5,6-diamino-1,3-dipropyluracil (1.81 g, 8 mmol) in dry pyridine (8.2 ml) maintained at 5° C. The reaction was warmed to room temperature and stirred for an additional 3 hours. Water (50 ml) was added to quench the reaction. The solvent was evaporated to afford a dark colored oil. The oil was refluxed for 2 h in 2N NaOH (20 ml). After cooling, the pH was carefully adjusted to 7 with concentrated HCl. A solid formed and was collected and washed with water (20 ml), ether (20 ml) and chloroform (20 ml) to provide an off-white solid (1.9 g). The product was used in the next step without further purification.

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. customto quench
  3. customthe reaction
  4. customThe solvent was evaporated
  5. customto afford a dark colored oil
  6. temperatureAfter cooling
  7. customA solid formed
  8. customwas collected
  9. washwashed with water (20 ml), ether (20 ml) and chloroform (20 ml)

Sources & evidence

ORD record
ord-f903e01985334e38bc5eaa7729ef0831
Source dataset
uspto-grants-2010_06
Patent number
US07732455B2

Reaction notes

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