Hydrochloric Acid → 2-Amino-6-chloro-9H-purine-9-acetic acid

HRID 50091

Reaction equation

HRID 50091 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([OH:22])=[O:21].Cl>CN(C=O)C.O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:19][C:20]([OH:22])=[O:21])=[C:4]([Cl:11])[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurine

Product 1

HCID 41928332-Amino-6-chloro-9H-purine-9-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-amino-6-chloropurine (5.02 g; 29.6 mmol) and potassium carbonate (12.91 g; 93.5 mmol) in DMF (50 ml) was added bromoacetic acid (4.70 g; 22.8 mmol). The mixture was stirred vigorously for 20 h. under nitrogen. Water (150 ml) was added and the solution was filtered through Celite to give a clear yellow solution. The solution was acidified to a pH of 3 with 4 N hydrochloric acid. The precipitate was filtered and dried, in vacuo, over sicapent. Yield (3.02 g; 44.8%). 1H-NMR(DMSO-d6): d=4.88 ppm (s,2H); 6.95 (s,2H); 8.10 (s,1H).

Workup

  1. filtrationthe solution was filtered through Celite
  2. customto give a clear yellow solution
  3. filtrationThe precipitate was filtered
  4. customdried, in vacuo
  5. customYield (3.02 g; 44.8%)

Sources & evidence

ORD record
ord-ef05ffb40df34eb2a3d154b30737afc3
Source dataset
uspto-grants-2004_03
Patent number
US06710163B1

Linked notes

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