Benzenamine, 3-ethynyl- → HCID 178436361, compound

HRID 1937386Notes

Reaction equation

HRID 1937386 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[NH2:11][C:12]1[CH:13]=[C:14]([C:18]#[CH:19])[CH:15]=[CH:16][CH:17]=1>N1C=CC=CC=1>[C:18]([C:14]1[CH:13]=[C:12]([NH:11][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH:17]=[CH:16][CH:15]=1)#[CH:19]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 53592776-Chloropurine

Product 1

HCID 178436361HCID 178436361, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To 6-chloropurine (1.0 g, 6.5 mmol) in dry pyridine (10 ml) was added m-aminophenyl acetylene (0.91 g, 7.8 mmol). The mixture was heated in an 85° C. oil bath for 23 hours. The mixture was cooled to ambient temperature and concentrated in vacuo. The oily residue was partitioned between CH2Cl2 and H2O then filtered to afford the title compound as a light orange solid (50 mg, 3.3%). LC-MS: 236 (MH+); anal. RP18-HPLC RT: 3.25 min.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe oily residue was partitioned between CH2Cl2 and H2O
  4. filtrationthen filtered

Sources & evidence

ORD record
ord-57691d5a18b944d79d0d1c3be4f7d71a
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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