3-Chloroaniline → HCID 23282755, compound

HRID 369836Notes

Reaction equation

HRID 369836 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[C:11]2[C:18]([CH3:19])=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N+:21]=3CC3C=CC=CC=3)[NH:16][C:12]=2[N:13]=[CH:14][N:15]=1>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][C:10]1[C:11]2[C:18]([CH3:19])=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[NH:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 23282756HCID 23282756, compound

Product 1

HCID 23282755HCID 23282755, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

With the exclusion of air, 529 μl (5.0 mmol) of 3-chloro-aniline are added to approximately 1.2 mmol of 4-chloro-5-methyl-6-(N-benzyl-pyridinium-2-yl)-7H-pyrrolo[2,3-d]-pyrimidine in 10 ml of isopropanol and the reaction mixture is boiled under reflux for 3 hours. The reaction mixture is concentrated by evaporation and the residue is chromatographed over silica gel. Elution with methylene chloride/ethanol (7:3) and methylene chloride/methanol (7:3) yields first 4-(3-chloro-anilino)-5-methyl-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (A) and then 4-(3-chloro-anilino)-5-methyl-6-(N-benzyl-pyridinium-2-yl)-7H-pyrrolo[2,3-d]pyrimidine bromide (B). A is also obtained by heating B. A: m.p. 251-252° C.; 1H-NMR (200 MHz, DMSO-d6): 12.75 and 9.25 (2sb), 8.75 (d, J=5, 1H), 8.35 (s, 1H), 8.05-7.85 (m, 3H), 7.66 (d, J=8, 1H), 7.45 (m, 2H), 7.29 (d, J=8, 1H), 2.84 (s, 3H); FAB-MS: (M+H)+ =336. B: m.p. 171-172° C. (intense foaming); 1H-NMR (200 MHz, DMSO-d6): 12.65 (sb), 9.48 (d, J=6, 1H), 8.80 (t, J=8, 1H), 8.59 (sb, 1H), 8.43 (s, 1H), 8.3 (m, 2H), 7.94 (m, 1H), 7.72 (d, J=8, 1H), 7.40 (t, J=8, 1H), 7.28 (m, 3H), 7.17 (d, J=8, 1H), 6.94 (m, 2H), 5.93 (s, 2H), 2.27 (s, 3H); FAB-MS: (M+H)+ =426.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. customthe residue is chromatographed over silica gel
  4. washElution with methylene chloride/ethanol (7:3) and methylene chloride/methanol (7:3)

Sources & evidence

ORD record
ord-a6d2e75864fa44e8a084fbfdd93fdb2c
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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