Ammonia → HCID 21949104, compound

HRID 2376895Notes

Reaction equation

HRID 2376895 reaction equation
[NH3:1].Cl[C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][NH:16]3)=[CH:12][CH:11]=2)[CH:4]=1>CO>[NH2:1][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][NH:16]3)=[CH:12][CH:11]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21949150HCID 21949150, compound

Product 1

HCID 21949104HCID 21949104, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A 7N ammonia in methanol solution (75 ml) was added to 6-chloro-4-(1H-6-indolylamino)pyrimidine (1.229 g, 5.0 mmol); and the reaction mixture was heated in a sealed tube at 130° C. for 6 days. 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 the residue to crystallize; the crystals were filtered off, and washed with diethyl ether, and dried under aeration to yield the title compound (883 mg, 3.9 mmol, 78%) as pale yellow 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 to the residue
  4. customto crystallize
  5. filtrationthe crystals were filtered off
  6. washwashed with diethyl ether
  7. customdried under aeration

Sources & evidence

ORD record
ord-6d37c5954caa42f99ba429cc19d190d8
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

Loading…