Benzenamine, 3-ethynyl- → HCID 22460853, compound

HRID 1937378Notes

Reaction equation

HRID 1937378 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C:18]#[CH:19])[CH:15]=[CH:16][CH:17]=1>N1C=CC=CC=1>[ClH:1].[C:18]([C:14]1[CH:13]=[C:12]([NH:11][C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:17]=[CH:16][CH:15]=1)#[CH:19]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 22460853HCID 22460853, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (10.0 g, 0.065 mol) in dry pyridine (90 ml) was added m-aminophenylacetylene (9.2 g, 0.078 mol), and the mixture was heated in an 85° C. oil bath for 2 days. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel (375 g, 40 μm mesh) using 5% methanol/CH2Cl2 to afford the title compound as a pink-orange solid (1.9 g, 12%). HRMS: Calcd. 235.0984, Found 235.1000; anal. RP18-HPLC RT: 3.48 min.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by flash chromatography on silica gel (375 g, 40 μm mesh)

Sources & evidence

ORD record
ord-1c93d5a9bd1c4b409171fa2c84322451
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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