Hydrochloric Acid → HCID 22174572, compound

HRID 1796967Notes

Reaction equation

HRID 1796967 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=O)[CH3:2].[NH2:13][C:14]1[C:15](=[O:24])[NH:16][C:17](=[O:23])[N:18]([CH2:21][CH3:22])[C:19]=1[NH2:20].C(N(CC)CC)C.[OH-].[Na+].Cl>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]1[NH:13][C:14]2[C:15](=[O:24])[NH:16][C:17](=[O:23])[N:18]([CH2:21][CH3:22])[C:19]=2[N:20]=1)[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 30163972-Ethoxybenzoyl chlorideHCID 219163605,6-Diamino-1-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 22174572HCID 22174572, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-ethoxybenzoyl chloride (12.0 g, 65 mmol) in dimethylformamide (10 mL) was added dropwise to a stirred solution of 5,6-diamino-1-ethyl-1H-pyrimidine-2,4-dione (10.4 g, 61 mmol) and triethylamine (9.8 mL, 65 mmol) in dimethylformamide (250 mL). The resulting mixture was stirred for 20 hours at room temperature, then evaporated under reduced pressure. Aqueous sodium hydroxide solution (1N, 98 mL, 98 mmol) was added and the mixture heated under reflux for 6 hours. The resulting solution was acidified with 1N hydrochloric acid and the precipitate collected and dried by suction to give 8-(2-ethoxyphenyl)-3-ethyl-3,7-dihydropurine-2,6-dione as a beige solid (7.0 g, 72%).

Workup

  1. customevaporated under reduced pressure
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 6 hours
  4. customthe precipitate collected
  5. customdried by suction

Sources & evidence

ORD record
ord-7bd6e8a5735e40f4b5d9c736bb189344
Source dataset
uspto-grants-2006_04
Patent number
US07034016B2

Reaction notes

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