Ammonia → HCID 21949139, compound

HRID 2376894Notes

Reaction equation

HRID 2376894 reaction equation
CO.[NH3:3].Cl[C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH:14]=[CH:15][NH:16]3)[CH:6]=1>O1CCCC1>[NH2:3][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH:14]=[CH:15][NH:16]3)[CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 21949160HCID 21949160, compound

Product 1

HCID 21949139HCID 21949139, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
130 °C

Procedure

A 7N methanol solution of ammonia (50 ml) and tetrahydrofuran (20 ml) were added to 6-chloro-4-(1H-4-indolylamino)pyrimidine (599 mg, 2.5 mmol) and the reaction mixture was heated in a sealed tube at 130° C. for 137 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 the residue to crystallize; the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (454 mg, 2.0 mmol, 82%) 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 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-b413b86c4afa4767b58e55a6421cf3a1
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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