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

HRID 50079

Reaction equation

HRID 50079 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 (4.7 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) δ: 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

Sources & evidence

ORD record
ord-45b943cbca4349939204f47c321c8cb1
Source dataset
uspto-grants-2004_03
Patent number
US06710164B1

Linked notes

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