Diisopropylethylamine → benzyl-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-ethyl-amine

HRID 1668835Notes

Reaction equation

HRID 1668835 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=2[N:3]=1.[CH2:12]([NH:19][CH2:20][CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>C(O)C>[CH2:12]([N:19]([C:6]1[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=2[N:3]=[C:2]([Cl:1])[N:7]=1)[CH2:20][CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 84352N-EthylbenzylamineHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidine

Product 1

HCID 59362933benzyl-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-ethyl-amineYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.4 g, 2.1 mmol), N-benzyl-ethylamine (0.35 mL, 2.3 mmol) and diisopropylethylamine (0.4 mL, 2.1 mmol) in anhydrous ethanol (5 mL) was heated at a temperature in the range of 20° C. to 90° C. for 18 hours. After cooling to about 20 to 35° C., the reaction mixture was concentrated under reduced pressure. The crude residue was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a light pink liquid (0.60 g, 98% yield).

Workup

  1. temperaturewas heated at a temperature in the range of 20° C. to 90° C. for 18 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe crude residue was diluted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e00028cc6cc4a17b9db62d21a41660a
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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