Potassium Carbonate → 2-Amino-6,8-dichloro-9-[1-(2,2-dimethyl-1,3-dioxane4,6-dione-5-yl)eth-2-yl]purine

HRID 846846Notes

Reaction equation

HRID 846846 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([Cl:11])=[N:8]2)=[C:4]([Cl:12])[N:3]=1.[CH3:13][C:14]1([CH3:24])[O:21][C:20](=[O:22])[C:17]2([CH2:19][CH2:18]2)[C:16](=[O:23])[O:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([Cl:11])[N:8]2[CH2:19][CH2:18][CH:17]2[C:16](=[O:23])[O:15][C:14]([CH3:24])([CH3:13])[O:21][C:20]2=[O:22])=[C:4]([Cl:12])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dioneHCID 54646776,8-Dichloro-9H-purin-2-amine

Product 1

HCID 198839932-Amino-6,8-dichloro-9-[1-(2,2-dimethyl-1,3-dioxane4,6-dione-5-yl)eth-2-yl]purineYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6,8-dichloropurine (2.04 g), 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (1.73 g) and anhydrous potassium carbonate (2.12 g) in N,N-dimethylformamide (40 ml) was stirred at room temperature for 18 hours under dry nitrogen. The solvent was evaporated and the residue dissolved in water (60 ml) and acidified from pH 10 to pH 4 with dilute hydrochloric acid. The yellow precipitate was filtered off, washed with water and dried to give 2-amino-6,8-dichloro-9-[1-(2,2-dimethyl-1,3-dioxane4,6-dione-5-yl)eth-2-yl]purine (2.2 g, 50%). T.1.c. r.f. 0.65 (25% methanol-dichloromethane).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water (60 ml)
  3. filtrationThe yellow precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b1a80c973d1042229fe8a2181048f816
Source dataset
uspto-grants-1992_08
Patent number
US05138057

Reaction notes

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