Ammonia → HCID 21949281, compound

HRID 2215565Notes

Reaction equation

HRID 2215565 reaction equation
[NH3:1].Cl[C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)[CH:4]=1>CO>[NH2:1][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)[CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21949278HCID 21949278, compound

Product 1

HCID 21949281HCID 21949281, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A 7N ammonia in methanol (60 ml) was added to 6-chloro-4-(1H-5-indolylamino)pyrimidine (2.455 g, 10 mmol); and the reaction mixture was heated in a sealed tube at 130° C. for 90 hours. The solvent was distilled off under reduced pressure; the residue was purified by silica gel column chromatography (eluent; ethyl acetate:tetrahydrofuran=1:1); diethyl ether was added to crystallize; and the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (1.563 g, 6.9 mmol, 69%) as pale brown crystals.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:tetrahydrofuran=1:1)
  3. additiondiethyl ether was added
  4. customto crystallize
  5. filtrationand the crystals were filtered off
  6. washwashed with diethyl ether
  7. customdried under aeration

Sources & evidence

ORD record
ord-5019e4d681364ead9b49242ad9c40995
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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