1-Butanol → 3-ethyl-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2,4(1H,3H)-pyrimidinedione

HRID 2106766Notes

Reaction equation

HRID 2106766 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH:28]=[CH:27][C:26](=[O:29])[N:25]([CH2:30][CH3:31])[C:24]2=[O:32])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+].C(O)CCC>O>[CH2:30]([N:25]1[C:26](=[O:29])[CH:27]=[CH:28][N:23]([C:20]2[CH:21]=[CH:22][C:17]([N:16]3[CH2:14][CH2:13][N:4]([C:5]4[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=4)[CH2:3][CH2:2]3)=[CH:18][CH:19]=2)[C:24]1=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 15064N,N-Bis(2-chloroethyl)-4-methoxybenzenamineHCID 516892Sodium BicarbonateHCID 151254801-(4-aminophenyl)-3-ethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 151254813-ethyl-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2,4(1H,3H)-pyrimidinedioneYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17.47 parts of N,N-bis(2-chloroethyl)-4-methoxybenzenamine, 16.3 parts of 1-(4-aminophenyl)-3-ethyl-2,4(1H,3H)-pyrimidinedione, 11.83 parts of sodium hydrogen carbonate and 240 parts of 1-butanol was stirred for 24 hours at reflux temperature. After cooling, 150 parts of water were added. The product was filtered off and crystallized from methylbenzene. The product was filtered off and dried in vacuo at 60° C., yielding 10.6 parts (37.0%) of 3-ethyl-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2,4(1H,3H)-pyrimidinedione; mp. 210.2° C. (int. 26).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationThe product was filtered off
  4. customcrystallized from methylbenzene
  5. filtrationThe product was filtered off
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-04af0ef3c5bf4c59bfa44976a3800235
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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