7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- → HCID 18473274, compound

HRID 2227247Notes

Reaction equation

HRID 2227247 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH2:17][N:18]2N)=[CH:14][CH:13]=1>N1C=CC=CC=1>[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH2:17][N:18]2[C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 18473294HCID 18473294, compound

Product 1

HCID 18473274HCID 18473274, compoundYield 6.3%

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 6chloro2,3dihydroindol-1-yl amine (14.8 g, 0.078 mol), and the mixture was heated in an 85° C. oil bath for 2 days. The reaction was cooled to ambient temperature and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel (375 g, 40 mm mesh) using 5% MeOH/CH2Cl2 to afford the title compound as a pink-orange solid (1.1 g, 4.3%): HRMS: Calculated 271.0750, Found 271.0729; anal. RP18-HPLC RT: 4.88 minutes.

Workup

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

Sources & evidence

ORD record
ord-9921b13ed0de42048b1b2a4a034a1992
Source dataset
uspto-grants-2002_07
Patent number
US06413971B1

Reaction notes

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