Aniline → HCID 10658048, compound

HRID 1884904Notes

Reaction equation

HRID 1884904 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 53244122,6-Dichloropurine

Product 1

HCID 10658048HCID 10658048, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,6-dichloropurine (20 g, 106 mmol) in 400 ml of ethanol are added 36.5 ml of aniline (400 mmol) and the resulting solution is kept at 50° C. under magnetic stirring for 12 h. After cooling to RT, the mixture is filtered, washed with 2×50 ml of ethanol and dried at 50° C. under HV to give 2-chloro-6-(phenyl-amino)-purine as a yellow powder (25.5 g, 104 mmoles) in 98% yield. Rf=0.57 (CH2Cl2/MeOH (95/5); m.p. decomp. >290° C.; ESI-MS: 246 (M+H)+; 1H—NMR (d6-DMSO, 200 MHz, TMS): 7.1 ppm (t, 1H, J=8 Hz, H6), 7.35 ppm (t, 2H, J=8 Hz, H5), 7.8 ppm (d, 2H, J=8 Hz, H4), 8.3 ppm (s, 1H, H2), 10.1 ppm (s, 1H, H3),

Workup

  1. customis kept at 50° C.
  2. filtrationthe mixture is filtered
  3. washwashed with 2×50 ml of ethanol
  4. customdried at 50° C. under HV

Sources & evidence

ORD record
ord-e3f4f1d5d66f4f3aa397b8d1ff27dbb7
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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