Hydrochloric Acid → HCID 23282691, compound

HRID 369857Notes

Reaction equation

HRID 369857 reaction equation
Cl.Br.[Cl:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[NH:7][C:8]1[C:9]2[C:16]([CH3:17])=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[NH:14][C:10]=2[N:11]=[CH:12][N:13]=1.[OH-].[Na+]>C(OCC)(=O)C>[ClH:3].[Cl:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[NH:7][C:8]1[C:9]2[C:16]([CH3:17])=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)[NH:14][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23282721HCID 23282721, compound

Product 1

HCID 23282691HCID 23282691, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

For the preparation of the HCl salt, 600 mg of 4-(3-chloro-anilino)-5-methyl-6-(4-hydroxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidine hydrobromide are dissolved while hot in 50 ml of ethyl acetate and at RT adjusted to pH 9.5 with 1 N NaOH and the organic phase is washed twice with water. The organic phase is dried and concentrated by evaporation, and the residue is dissolved in 30 ml of ethanol, and a 5N (=5 normal) ethanolic HCl solution is added thereto. At 0° C., with stirring and the addition of diethyl ether, 4-(3-chloro-anilino)-5-methyl-6-(4-hydroxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine hydrochloride is obtained in the form of a colourless powder having a m.p. of 280-282° C.

Workup

  1. customat RT
  2. washthe organic phase is washed twice with water
  3. customThe organic phase is dried
  4. concentrationconcentrated by evaporation
  5. dissolutionthe residue is dissolved in 30 ml of ethanol
  6. additiona 5N (=5 normal) ethanolic HCl solution is added
  7. additionthe addition of diethyl ether

Sources & evidence

ORD record
ord-e0f279993fce413cb16165e4d9d03e19
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

Loading…