1,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione → HCID 19898755, compound

HRID 1196726Notes

Reaction equation

HRID 1196726 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH:20]4[O:22][CH2:21]4)[C:10]=3[C:11](=[O:13])[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][N:24]1[C:29]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:28][C:27](=[O:36])[N:26]([CH3:37])[C:25]1=[O:38]>C(O)C>[CH3:23][N:24]1[C:29]([N:30]2[CH2:35][CH2:34][N:33]([CH2:21][CH:20]([OH:22])[CH2:19][O:18][C:14]3[C:10]4[C:11](=[O:13])[CH:12]=[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[O:8][C:9]=4[CH:17]=[CH:16][CH:15]=3)[CH2:32][CH2:31]2)=[CH:28][C:27](=[O:36])[N:26]([CH3:37])[C:25]1=[O:38]

Participants

4

Reactant 2

HCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 14626344HCID 14626344, compound2×

Product 1

HCID 19898755HCID 19898755, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 30 ml of ethanol, there were heated under reflux for 3 hours 0.88 g of 2-phenyl-5-(2,3-epoxypropoxy)-4-oxo-4H-1-benzopyran (Compound 36) and 0.67 g of 1,3-dimethyl-6-(piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (Compound 3), and the reaction solution was then concentrated under reduced pressure. The resultant residue was purified through a silica gel column chromatograph (chloroform:methanol=100:1 to 100:5 in volume ratio), and then crystallized from ethyl acetate, thereby obtaining 1.21 g of 1,3-dimethyl-6-(4-[3-(2-phenyl-4-oxo-4H-1-benzopyran-5-yl)oxy-2-hydroxypropyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the non-hydrochloride of Compound 37).

Workup

  1. concentrationthe reaction solution was then concentrated under reduced pressure
  2. customThe resultant residue was purified through a silica gel column chromatograph (chloroform:methanol=100:1 to 100:5 in volume ratio)
  3. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bb8f099aafa24846a4900454951c99fc
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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