Potassium Carbonate → HCID 21278111, compound

HRID 2291852Notes

Reaction equation

HRID 2291852 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+].[CH2:18]([O:25][CH2:26][C:27]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[CH:28][CH2:29]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:29][CH:28]=[C:27]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:26][O:25][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurineHCID 21278117HCID 21278117, compound

Product 1

HCID 21278111HCID 21278111, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 1.61 g 2-amino-6-chloropurine (9.5 mmol) and 1.31 g finely ground anhydrous K2CO3 (9.5 mmol) in 50 ml of dry dimethylformamide (DMF) was kept at 100° C. for 5 min. and cooled. At 10° C. the crude 1-benzyloxy-2-benzyloxymethyl-4-chlorobut-2-ene in 25 ml of dry DMF was added with stirring during 4 h. After 2 days at room temperature the mixture was evaporated in vacuum, the residue was extracted with 2×25 ml of chloroform and the extract evaporated to dryness. Chromatography (silica gel, CHCl3 +MeOH 19+1) afforded 0.25 g (18%) of 4-(2-amino-6-chloropurin-9-yl)-1-benzyloxy-2-benzyloxymethyl-2-butene (TLC on silica gel, CHCl3 +MeOH 13+1 parts by volume Rf 0.62).

Workup

  1. temperaturecooled
  2. customAfter 2 days at room temperature the mixture was evaporated in vacuum
  3. extractionthe residue was extracted with 2×25 ml of chloroform
  4. customthe extract evaporated to dryness

Sources & evidence

ORD record
ord-e1aff22c3dbc4b9c8249a8ba4cf22a08
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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