Propylamine → [2-(4-Phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]propylamine

HRID 2240102Notes

Reaction equation

HRID 2240102 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]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1.[CH2:23]([NH2:26])[CH2:24][CH3:25]>O>[C:14]1([N:11]2[CH2:12][CH2:13][N:8]([C:6]3[N:7]=[C:2]([CH2:25][CH2:24][CH2:23][NH2:26])[C:3]4[S:22][CH2:21][CH2:20][C:4]=4[N:5]=3)[CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 866162644-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 68440117[2-(4-Phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]propylamineYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.83 g (2.5 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V) is combined with 8.3 mL of n-propylamine, reacted for 0.2 hours at 130° C. in the microwave. Then the reaction mixture is added to water and extracted with dichloromethane. The organic phase is concentrated by evaporation, the residue is crystallized. The aqueous phase is extracted with ethyl acetate, the organic phase evaporated to dryness. The solids are combined and stirred with methanol. 0.68 g of the product (76%) is obtained as a powder.

Workup

  1. customreacted for 0.2 hours at 130° C. in the microwave
  2. extractionextracted with dichloromethane
  3. concentrationThe organic phase is concentrated by evaporation
  4. customthe residue is crystallized
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. customthe organic phase evaporated to dryness

Sources & evidence

ORD record
ord-2bd13a201dbd4e83b06b926bab1a630e
Source dataset
uspto-grants-2010_05
Patent number
US07723341B2

Reaction notes

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