Diethyl Ether → 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1729275Notes

Reaction equation

HRID 1729275 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][C:5](=[O:14])[N:4]([CH3:15])[C:3]1=[O:16].Br[CH2:18][CH2:19][CH2:20][OH:21].C(N(CC)CC)C.CCOCC>C(O)C>[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:18][CH2:19][CH2:20][OH:21])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:14])[N:4]([CH3:15])[C:3]1=[O:16]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 123083-Bromo-1-propanolHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 103564171,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

14.1 g of 1,3-dimethyl-6-(1-piperazinyl)-2,4(1H,3H)-pyrimidinedione (compound b), 11.7 g of 3-bromo-1-propanol and 13 g of triethylamine were heated under reflux in 250 ml of ethanol for 20 hours to carry out reaction. After completion of the reaction, the resultant reaction mixture was then concentrated to dryness, and the resultant residue was dissolved in 300 ml of chloroform and then washed with 100 ml of water twice. The washed organic layer was dried over anhydrous magnesium sulfate and then treated with under reduced pressure, and the solvent was distilled off, thereby obtaining 20.5 g of a crude product. Next, ether was added to this crude product so as to achieve crystallization. The resultant crystals were recovered, washed and then dried to obtain 12.4 g (yield 69.8%) of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound a).

Workup

  1. customreaction
  2. customAfter completion of the reaction
  3. customthe resultant reaction mixture
  4. concentrationwas then concentrated to dryness
  5. dissolutionthe resultant residue was dissolved in 300 ml of chloroform
  6. washwashed with 100 ml of water twice
  7. dry with materialThe washed organic layer was dried over anhydrous magnesium sulfate
  8. additiontreated with under reduced pressure
  9. distillationthe solvent was distilled off
  10. customobtaining 20.5 g of a crude product
  11. customcrystallization
  12. customThe resultant crystals were recovered
  13. washwashed
  14. customdried

Sources & evidence

ORD record
ord-cf7899b4daba42128b0d0ce1d47c0936
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

Loading…