Benzenamine, 3-ethynyl- → HCID 18473271, compound

HRID 2227253Notes

Reaction equation

HRID 2227253 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH2:11][CH:12]=[CH2:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:14][C:15]1[CH:16]=[C:17]([C:21]#[CH:22])[CH:18]=[CH:19][CH:20]=1>CO>[CH2:11]([N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[CH:22])[CH:16]=3)[C:3]=2[CH:10]=[CH:9]1)[CH:12]=[CH2:13]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 184732904-Chloro-7-(prop-2-en-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 18473271HCID 18473271, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

To 4-chloro-7-allyl-pyrrolo[2,3-d]pyrimidine (0.5 g, 2.6 mmol) in dry MeOH (5 ml) was added m-aminophenyl acetylene (0.36 g, 3.1 mmol). The suspension was heated in a sealed pressure tube at 125° C. for 20 hours. The reaction was cooled to ambient temperature and concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel (50 g, 40 mm mesh) using 3% MeOH/CH2Cl2 to afford the title compound as a yellow powder (0.29 g, 41%): TS-MS: 275 (MH+); anal. RP18-HPLC RT: 4.62 minutes.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was purified by flash chromatography on silica gel (50 g, 40 mm mesh)

Sources & evidence

ORD record
ord-add69a27f20d4b05a9355d97e783fa64
Source dataset
uspto-grants-2002_07
Patent number
US06413971B1

Reaction notes

Loading…