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

HRID 1805972Notes

Reaction equation

HRID 1805972 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:12]([NH2:15])[CH2:13][CH3:14].C(N(C(C)C)C(C)C)C>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH2:14][CH2:13][CH2:12][NH2:15])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 86632801(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamineYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.4 g (50.2 mmol) of 2,4-dichlorothieno[3,2-d]pyrimidine (VII), 8.2 mL (100 mmol) of N-propylamine, and 17.5 mL (100 mmol) of N-ethyldiisopropylamine are placed in 100 mL of tetrahydrofuran and stirred for 20 hours at ambient temperature. The suspension is filtered, the filtrate is concentrated by evaporation. The residue is combined with 100 mL of water and treated in the ultrasound bath. Solid substance is suction filtered, dried, and stirred with 50 mL of petroleum ether. 10.0 g of the product VIII (86%) is obtained as a powder.

Workup

  1. filtrationThe suspension is filtered
  2. concentrationthe filtrate is concentrated by evaporation
  3. additiontreated in the ultrasound bath
  4. filtrationfiltered
  5. customdried
  6. stirringstirred with 50 mL of petroleum ether

Sources & evidence

ORD record
ord-dac3cef3c5ff4010a7ab817947fa74cc
Source dataset
uspto-grants-2013_01
Patent number
US08354531B2

Reaction notes

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