Chloroform → 9-(1,3-Diacetoxy-2-propoxymethyl)-2-amino-6-chloropurine

HRID 330588Notes

Reaction equation

HRID 330588 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.[H-].[Na+].[C:14]([O:17][CH2:18][CH:19]([O:25][CH2:26]Cl)[CH2:20][O:21][C:22](=[O:24])[CH3:23])(=[O:16])[CH3:15].C(Cl)(Cl)Cl>CN(C)C=O.O.CO>[C:22]([O:21][CH2:20][CH:19]([O:25][CH2:26][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[Cl:11])[CH2:18][O:17][C:14](=[O:16])[CH3:15])(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 24758Sodium hydrideHCID 53603492-Amino-6-chloropurineHCID 19868843Chloromethyl 1,3-Diacetoxy-2-propyl Ether

Product 1

HCID 137128349-(1,3-Diacetoxy-2-propoxymethyl)-2-amino-6-chloropurineYield 7.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 1.44 g (8.53 mmoles) of 2-amino-6-chloropurine in 34 ml of anhydrous dimethylformamide under a nitrogen blanket was treated with 203 mg (8.53 mmoles, 340 mg of 60% dispersion in mineral oil) of sodium hydride. After twenty minutes the reaction mixture became a solution and 1.92 g (8.53 mmoles) of chloromethyl 1,3-diacetoxy-2-propyl ether in about 7 ml of anhydrous dimethylformamide was added. The reaction was monitored by t.1.c. on silica in a 90:10:1 (CHCl3 :CH3OH:H2O) system to observe disappearance of the side chain precursor. After about two hours the reaction mixture was filtered and concentrated to a cloudy oil in vacuo. The oily product had solidified upon standing and was triturated with ether. The product was isolated by filtration, washed with ether then water, again with ether, and finally dried in vacuo over P2O5 yielding 1.4 g of product. An additional 220 mg of product was obtained by filtration after the ether washes were concentrated to a small volume.

Workup

  1. waitAfter twenty minutes the reaction mixture became
  2. filtrationAfter about two hours the reaction mixture was filtered
  3. concentrationconcentrated to a cloudy oil in vacuo
  4. customwas triturated with ether
  5. customThe product was isolated by filtration
  6. washwashed with ether
  7. dry with materialwater, again with ether, and finally dried in vacuo over P2O5 yielding 1.4 g of product

Sources & evidence

ORD record
ord-b36e292fddec45ff9655f80e9b531498
Source dataset
uspto-grants-1990_01
Patent number
US04897479

Reaction notes

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