4-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine → (2-Piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine

HRID 1788013Notes

Reaction equation

HRID 1788013 reaction equation
Cl[C:2]1[C:3]2[S:22][CH2:21][CH2:20][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11](C3C=CC=CC=3)[CH2:10][CH2:9]2)[N:7]=1.[CH:23]1([NH:29]C2C3SCCC=3N=C(N3CCN(C4C=CC(C(OCC)=O)=CC=4)CC3)N=2)CCC[CH2:25][CH2:24]1>O1CCOCC1>[N:8]1([C:6]2[N:7]=[C:2]([CH2:25][CH2:24][CH2:23][NH2:29])[C:3]3[S:22][CH2:21][CH2:20][C:4]=3[N:5]=2)[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 866162644-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidineHCID 86616266Ethyl 4-[4-(4-cyclohexylamino-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]benzoate

Product 1

HCID 68438559(2-Piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamineYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 g (4.4 mmol) of (2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine (V) and 1.9 g (21.8 mmol) of piperazine (VI) are placed in 10 mL of dioxane, then reacted for 0.7 hours at 150° C. in the microwave. Then the reaction mixture is extracted with water and ethyl acetate, and the organic phase is dried and evaporated to dryness. The residue is triturated with petroleum ether and suction filtered. 0.97 g of product VII (80%) is obtained as a powder.

Workup

  1. customreacted for 0.7 hours at 150° C. in the microwave
  2. extractionThen the reaction mixture is extracted with water and ethyl acetate
  3. customthe organic phase is dried
  4. customevaporated to dryness
  5. customThe residue is triturated with petroleum ether and suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-23e22e80c1564ca08293ef3f42cc469e
Source dataset
uspto-grants-2009_03
Patent number
US07511045B2

Reaction notes

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