Benzenamine, 3-ethynyl- → HCID 22460847, compound

HRID 1937401Notes

Reaction equation

HRID 1937401 reaction equation
[Cl:1][C:2]1[C:7]2N(C)CC[C:6]=2[N:5]=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([C:19]#[CH:20])[CH:16]=[CH:17][CH:18]=1>CO>[ClH:1].[C:19]([C:15]1[CH:14]=[C:13]([NH:12][C:6]2[C:7]3[C:7]([CH3:6])=[CH:2][NH:3][C:2]=3[N:3]=[CH:4][N:5]=2)[CH:18]=[CH:17][CH:16]=1)#[CH:20]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 86758098HCID 86758098, compound

Product 1

HCID 22460847HCID 22460847, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

To 4-chloro5-methyl-7H-pyrrolopyrimidine (0.17 g, 1.0 mmol) in dry methanol (3 ml) was added m-aminophenyl acetylene (0.14 g, 1.2 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 residue was purified by flash chromatography on silica gel (15 g,40 mm mesh) using 5% methanol/methylene chloride to afford the title compound as a yellow solid (0.11 g, 43%). TS-MS: 249 (MH+); anal. RP18-HPLC RT: 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 (15 g,40 mm mesh)

Sources & evidence

ORD record
ord-ca92969d8bc44e40bc67a3e6a43df1d4
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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