1-Benzylpiperazine → 6-Methyl-5-[4-(phenylmethyl)-1-piperazinyl]-2,4(1H,3H)-pyrimidinedione

HRID 371454

Reaction equation

HRID 371454 reaction equation
Br[C:2]1[C:3](=[O:10])[NH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].O.O.[F-].[K+].[CH2:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:8][C:7]1[NH:6][C:5](=[O:9])[NH:4][C:3](=[O:10])[C:2]=1[N:25]1[CH2:26][CH2:27][N:22]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 759941-BenzylpiperazineHCID 847572,4(1H,3H)-Pyrimidinedione, 5-bromo-6-methyl-HCID 23708904Potassium fluoride dihydrate

Product 1

HCID 134783296-Methyl-5-[4-(phenylmethyl)-1-piperazinyl]-2,4(1H,3H)-pyrimidinedione

Procedure

A mixture of 20.5 g (0.10 mole) of 5-bromo-6-methyl-2,4(1H,3H)pyrimidinedione and 10.3 g (0.11 mole) of potassium fluoride dihydrate in 130 ml of 1-benzylpiperazine was heated under reflux for 72 hours. The reaction mixture was then cooled and poured into 800 ml of ice water. The solid which formed was collected and washed with water to give 8.10 g of the product as an off-white solid. A 1.0 g portion of the crude product was recrystallized from methanol to give an off-white solid, mp 263° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 hours
  3. temperatureThe reaction mixture was then cooled
  4. customThe solid which formed
  5. customwas collected
  6. washwashed with water

Sources & evidence

ORD record
ord-b268680494234b9691676094c3fcf777
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Linked notes

Loading…