6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione → HCID 19045534, compound

HRID 1781394Notes

Reaction equation

HRID 1781394 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][C:9](=[O:18])[C:8]=2[CH:19]=1.Cl[C:21]1[N:26]([CH3:27])[C:25](=[O:28])[N:24]([CH3:29])[C:23](=[O:30])[CH:22]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:11]3([CH2:12][CH2:13][N:14]([C:21]4[N:26]([CH3:27])[C:25](=[O:28])[N:24]([CH3:29])[C:23](=[O:30])[CH:22]=4)[CH2:15][CH2:16]3)[CH2:10][C:9](=[O:18])[C:8]=2[CH:19]=1

Participants

5

Reactant 3

HCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedioneHCID 516892Sodium BicarbonateHCID 45158372HCID 45158372, compound

Product 1

HCID 19045534HCID 19045534, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3,4-dihydro-6-methoxyspiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one hydrochloride (0.568 g, 2 mmol), 6-chloro-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione (0.349 g, 2 mmol) and sodium bicarbonate (0.42 g, 5 mmol) in acetonitrile was heated at reflux for 42 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 twice with water and once with saturated brine solution and then dried over sodium sulfate and concentrated to dryness in vacuo. The solid residue was recrystallized from methanol/ethanol to give the title compound (0.47 g, 61% yield) mp 202°-203° C.

Workup

  1. temperatureat reflux for 42 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo to dryness
  4. customThe residue was partitioned between chloroform and water
  5. washThe chloroform solution was washed twice with water and once with saturated brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness in vacuo
  8. customThe solid residue was recrystallized from methanol/ethanol

Sources & evidence

ORD record
ord-5316fdb95ac1472fad8e43ff4c6050cf
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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