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

HRID 2227703Notes

Reaction equation

HRID 2227703 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-55a1387963334c25884c1bd6791b7dc2
Source dataset
uspto-grants-2002_07
Patent number
US06414112B1

Reaction notes

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