6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione → HCID 19045431, compound

HRID 1781395Notes

Reaction equation

HRID 1781395 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:16][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH2:9][C:8](=[O:17])[C:7]=2[CH:18]=1.C(=O)(O)[O-].[Na+].Cl.Cl[CH2:26][CH2:27][NH2:28].Cl[C:30]1[N:35]([CH3:36])[C:34](=[O:37])[N:33]([CH3:38])[C:32](=[O:39])[CH:31]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:16][C:10]3([CH2:11][CH2:12][N:13]([NH:28][CH2:27][CH2:26][C:30]4[N:35]([CH3:36])[C:34](=[O:37])[N:33]([CH3:38])[C:32](=[O:39])[CH:31]=4)[CH2:14][CH2:15]3)[CH2:9][C:8](=[O:17])[C:7]=2[CH:18]=1

Participants

6

Reactant 4

HCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedioneHCID 516892Sodium Bicarbonate2×HCID 97937372-Chloroethylamine hydrochlorideHCID 16643157HCID 16643157, compound

Product 1

HCID 19045431HCID 19045431, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3,4-dihydro-6-methoxyspiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one (0.284 g, 1 mmol) and sodium bicarbonate (0.42 g, 5 mmol) in acetonitrile was heated at reflux for 1 hour, 2-chloro ethylamine hydrochloride (0.116 g, 1 mmol) was added the solution was heated at reflux for 17 hours, 6-chloro-1,3-dimethyluracil (0.175 g, 1 mmol) and sodium bicarbonate (0.16 g, 2 mmol) were added. Refluxing was continued for 28 hours. After cooling, the reaction mixture was concentrated in vacuo to dryness. The residue was partitioned between chloroform and water. The chloroform solution was washed with water and dried over sodium sulfate. The resulting residue was chromatographed through a pressure column (silica gel) eluting with 5% methanol/chloroform to give the title compound (45 mg, 10.5% yield), mp 235°-238° C. dec.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperaturewas heated
  4. temperatureat reflux for 17 hours
  5. temperatureRefluxing
  6. temperatureAfter cooling
  7. concentrationthe reaction mixture was concentrated in vacuo to dryness
  8. customThe residue was partitioned between chloroform and water
  9. washThe chloroform solution was washed with water
  10. dry with materialdried over sodium sulfate
  11. customThe resulting residue was chromatographed through a pressure column (silica gel)
  12. washeluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-88c9f74d06f8450f9794988fded824ed
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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