Tert-Butylamine → tert-butyl-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-amine

HRID 1668821Notes

Reaction equation

HRID 1668821 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.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>C(O)(C)C>[C:12]([NH:16][C:6]1[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=2[N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidine

Product 1

HCID 59362934tert-butyl-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-amineYield 64%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.47 g, 2.5 mmol), tert-butylamine (1.25 ml, 11.8 mmol) and isopropanol (5 ml) was heated at reflux for 8 to 18 hours. After evaporation of volatiles the mixture was purified by flash chromatography over silica gel to afford the title compound as a white solid (0.36 g, 64% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 to 18 hours
  3. customAfter evaporation of volatiles the mixture
  4. customwas purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-60d58cbc72104665b9b026096bffed4e
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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