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

HRID 1788007Notes

Reaction equation

HRID 1788007 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-a2b6d00b91ba48a797feb875d86c2175
Source dataset
uspto-grants-2009_03
Patent number
US07511045B2

Reaction notes

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