Sodium Iodide → 3-[5-[4-(2-Methoxyphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]-pyrimidine-2,4-dione

HRID 2165196Notes

Reaction equation

HRID 2165196 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[C:15]([C:16]([O:18]C)=O)=[CH:14][S:13][CH:12]=1)=[O:9].Cl.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[Na+].[I-].C([O-])(O)=O.[Na+].[OH-].[Na+]>CC(O)C.O>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]2[C:16](=[O:18])[C:15]3=[CH:14][S:13][CH:12]=[C:11]3[NH:10][C:8]2=[O:9])[CH2:31][CH2:30]1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 15697668N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl)urea

Product 1

HCID 156976693-[5-[4-(2-Methoxyphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]-pyrimidine-2,4-dioneYield 109.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

The above urea (8.0 g, 23 mmol) was reacted with 1-(2-methoxyphenyl)piperazine hydrochloride (10.48 g, 45 mmol), NaI (1.72 g, 11 mmol) and NaHCO3 (7.69 g, 92 mmol) in 50 mL of 2-propanol at reflux for 6 hours under a nitrogen blanket. After cooling, water was added and the 2-propanol was removed by distillation. The brown residue was dissolved in CH2Cl2 and washed with water and brine and dried (MgSO4). After the solvent has been removed in vacuo, the tan residue was dissolved in MeOH and treated with 1.1 equivalents of 50% NaOH and the solution was refluxed for 3.5 hours. The pH of the solution was adjusted to 6 with 2N HCL and the methanol was removed by distillation. The resulting oil was dissolved in CH2Cl2 and washed with water and brine and dried (MgSO4). Solvent removal produced 10.81 g (91%) of 3-[5-[4-(2-methoxyphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione which was crystallized from CH2Cl2 /ether to afford a tan solid, mp 148°-153° C.

Workup

  1. temperatureat reflux for 6 hours under a nitrogen blanket
  2. temperatureAfter cooling
  3. customthe 2-propanol was removed by distillation
  4. dissolutionThe brown residue was dissolved in CH2Cl2
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. customAfter the solvent has been removed in vacuo
  8. dissolutionthe tan residue was dissolved in MeOH
  9. temperaturethe solution was refluxed for 3.5 hours
  10. customthe methanol was removed by distillation
  11. dissolutionThe resulting oil was dissolved in CH2Cl2
  12. washwashed with water and brine
  13. dry with materialdried (MgSO4)
  14. customSolvent removal

Sources & evidence

ORD record
ord-980c0d2190f046c19db637afbef5c3ef
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

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