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

HRID 567756Notes

Reaction equation

HRID 567756 reaction equation
O[Li].[OH2:3].[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:19]=[C:18](OCC)[NH:17][C:11]=2[NH:12][C:13](=C=O)[N:14]=1.Cl.[CH3:27][OH:28]>O>[C:27]([C:18]1[NH:17][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:19]=1)([OH:28])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 1765196754-(3-chloroanilino)-6-ethoxy-carbonyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 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-chloroanilino)-6-ethoxy-carbonyl-7H-pyrrolo[2,3-d]pyrimidine (see stage1.4) in 0.7 ml of methanol and the mixture is heated to boiling for 4.5 h. It is cooled in an ice bath and acidified with 0.6 ml of 1 normal HCl solution. Filtering off and washing with water yields 6-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=8.7; FAB-MS: (M+H)+=289.

Workup

  1. temperaturethe mixture is heated
  2. temperatureIt is cooled in an ice bath
  3. filtrationFiltering off
  4. washwashing with water

Sources & evidence

ORD record
ord-b9143c73542147fba59832036551e43c
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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