Potassium Carbonate → 2-Amino-6,8-dichloro-9-(2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl)purine

HRID 846847

Reaction equation

HRID 846847 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.Br[CH2:14][CH2:15][CH:16]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]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[CH2:14][CH2:15][CH:16]2[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]2)=[C:4]([Cl:12])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1789881,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-HCID 54646776,8-Dichloro-9H-purin-2-amine

Product 1

HCID 198839912-Amino-6,8-dichloro-9-(2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl)purineYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6,8-dichloropurine (0.82 g), 5-bromoethyl-2,2-dimethyl-1,3-dioxan (0.9 g) and anhydrous potassium carbonate (0.83 g) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 18 hours under dry nitrogen. The mixture was then filtered and the filtrate evaporated. The residue was purified by column chromatography on silica (100 g) [eluent 2% methanol-dichloromethane] to give 2-amino-6,8-dichloro-9-(2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl)purine (t.l.c. r.f. 0.50, 5% methanol-dichloromethane) as a pale solid (0.62 g, 45%). Recrystallisation from diethyl ether gave an off-white solid m.p. 149°-150° C.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated
  3. customThe residue was purified by column chromatography on silica (100 g) [eluent 2% methanol-dichloromethane]

Sources & evidence

ORD record
ord-a403aacc28a742d09c1c39cdb24ddfc7
Source dataset
uspto-grants-1992_08
Patent number
US05138057

Linked notes

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