Potassium Carbonate → HCID 19833364, compound

HRID 2051363Notes

Reaction equation

HRID 2051363 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([S:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[C:25]([O:28][CH2:29][CH:30]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH2:31][CH2:32]I)(=[O:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:25]([O:28][CH2:29][CH:30]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH2:31][CH2:32][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[S:11][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1539121,3-Propanediol, 2-(2-iodoethyl)-, diacetateHCID 21823366HCID 21823366, compound

Product 1

HCID 19833364HCID 19833364, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6-[(diphenylmethyl)thio]purine (6.7 g), 2-acetoxymethyl-4-iodobut-1-yl acetate (7.0 g) and anhydrous potassium carbonate (4.14 g) in N,N-dimethylformamide (100 cm3) was stirred at ambient temperature overnight. The reaction mixture was filtered and the residue washed with N,N-dimethylformamide (100 cm3). Evaporation of the filtrate gave a pale coloured oil. Purification via column chromatography on silica (450 g) [eluant 3% methanol-dichloromethane] gave the title compound 9.3 g (89%) as a viscous gum and 1.1 g (10.5%) of 7-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-(diphenylmethyl)thio]purine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with N,N-dimethylformamide (100 cm3)
  3. customEvaporation of the filtrate
  4. customgave a pale coloured oil
  5. customPurification via column chromatography on silica (450 g) [eluant 3% methanol-dichloromethane]

Sources & evidence

ORD record
ord-6eed3b35c7fa4621b27a8652a43dcbca
Source dataset
uspto-grants-1991_05
Patent number
US05017701

Reaction notes

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