Hydrochloric Acid → 4-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine hydrochloride

HRID 369834Notes

Reaction equation

HRID 369834 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 99490364-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 232827524-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.48 g (4.6 mmol) of 4-(3-chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (see Example 1) are suspended in 115 ml of dioxane; with cooling, 46 ml of 0.1 N HCl solution (0.1 normal hydrochloric acid solution) are added and the reaction suspension is stirred at RT for 2.5 hours. The suspension is concentrated by evaporation and the residue is stirred in 400 ml of hot methanol and filtered. The filtrate is filtered while hot through activated carbon, concentrated by evaporation and digested in cold ethanol; m.p. 276-278° C.; 1H-NMR (200 MHz, DMSO-d6): 13.1 and 10.7 (2s, 2H), 8.71 (d, J=5, 1H), 8.45 and 8.08 (2s, 2H), 8.00 (m, 2H), 7.76 (d, J=8, 1H), 7.68 (s, 1H), 7.50 (d, J=8, 1H), 7.42 (m, 1H), 7.27 (d, J=8, 1H).

Workup

  1. temperaturewith cooling
  2. concentrationThe suspension is concentrated by evaporation
  3. stirringthe residue is stirred in 400 ml of hot methanol
  4. filtrationfiltered
  5. filtrationThe filtrate is filtered while hot
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-213ad08d77474bb5947fc89de0315fbf
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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