Benzenamine, 3-ethynyl- → HCID 22460872, compound

HRID 1937399Notes

Reaction equation

HRID 1937399 reaction equation
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([C:19]#[CH:20])[CH:16]=[CH:17][CH:18]=1>CO>[Br:1][C:2]1[C:10]2[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[CH:20])[CH:14]=3)=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 22460872HCID 22460872, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

To 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.13 g, 0.57 mmol) in dry methanol (2 ml) was added m-aminophenyl acetylene (0.08 g, 0.68 mmol). The suspension was heated in a sealed pressure tube at 125° C. for 18 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel (10 g, 40 mm mesh) using 3% methanol/methylene chloride to afford the title compound as a yellow powder (71 mg, 39%). TS-MS: 314 (MH+); anal. RP18-HPLC RT: min.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was purified by flash chromatography on silica gel (10 g, 40 mm mesh)

Sources & evidence

ORD record
ord-cbe056b4c3a8499d8967f987c6f67007
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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