1-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine → 3,4,5,7-Tetrahydro-6-carbethoxy-3-[2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl]pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidin-4-one

HRID 276818Notes

Reaction equation

HRID 276818 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6][CH2:5]1.C(O[CH:21]=[N:22][C:23]1[S:30][C:29]2[CH2:28][N:27]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:26][C:25]=2[C:24]=1[C:36](OCC)=[O:37])C>C(O)C>[C:31]([N:27]1[CH2:28][C:29]2[S:30][C:23]3[N:22]=[CH:21][N:1]([CH2:2][CH2:3][N:4]4[CH2:5][CH2:6][N:7]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=5[O:16][CH3:17])[CH2:8][CH2:9]4)[C:36](=[O:37])[C:24]=3[C:25]=2[CH2:26]1)([O:33][CH2:34][CH3:35])=[O:32]

Participants

4

Reactant 2

HCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazineHCID 544107892-Ethoxymethyleneamino-3,5-dicarbethoxy-4,6-dihydrothieno[3,2-c]pyrrole

Product 1

HCID 154071263,4,5,7-Tetrahydro-6-carbethoxy-3-[2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl]pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidin-4-oneYield 48.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.1 g (4.8 mM) of 1-(2-aminoethyl)-4-(2-methoxyphenyl)-piperazine were added to 1.6 g (4.8 mM) of 2-ethoxymethyleneamino-3,5-dicarbethoxy-4,6-dihydrothieno[3,2-c]pyrrole in 25 ml of ethanol and refluxed for 2 h. The mixture was then concentrated in a rotary evaporator, and the crude product was purified by column chromatography (silica gel, mobile phase methylene chloride/methanol 96/4). After recrystallization from ethyl acetate, 1.1 g (47%) of product were isolated with melting point 153-155° C.

Workup

  1. temperaturerefluxed for 2 h
  2. concentrationThe mixture was then concentrated in a rotary evaporator
  3. customthe crude product was purified by column chromatography (silica gel, mobile phase methylene chloride/methanol 96/4)
  4. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4448ccf54300443883f8be758cfa0479
Source dataset
uspto-grants-2002_03
Patent number
US06355647B1

Reaction notes

Loading…