Hydrochloric Acid → 6-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369867Notes

Reaction equation

HRID 369867 reaction equation
O[Li].O.[Cl:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[NH:8][C:9]1[C:10]2[CH:17]=[C:16]([C:18]([O:20]CC)=[O:19])[NH:15][C:11]=2[N:12]=[CH:13][N:14]=1.Cl>O.CO>[C:18]([C:16]1[NH:15][C:11]2[N:12]=[CH:13][N:14]=[C:9]([NH:8][C:7]3[CH:23]=[CH:24][CH:25]=[C:5]([Cl:4])[CH:6]=3)[C:10]=2[CH:17]=1)([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 212626224-(3-chloroanilino)-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 212626746-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 25 mg (0.6 mmol) of LiOH.H2O in 0.4 ml of H2O is added dropwise to a suspension of 95 mg (0.30 mmol) of 4-(3-chloro-anilino)-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine in 0.7 ml of methanol. The reaction mixture is heated at boiling for 4.5 hours, then cooled in an ice-bath and acidified with 0.6 ml of 1 N HCl solution. Filtering and washing with water yield the title compound; HPLC: tRet (Grad20)=8.7; FAB-MS: (M+H)+ =289.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperaturecooled in an ice-bath
  3. filtrationFiltering
  4. washwashing with water

Sources & evidence

ORD record
ord-6e5c5a67cccb48f69011ecd95f619f94
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

Loading…