Sodium Carbonate → HCID 66671626, compound

HRID 2278869Notes

Reaction equation

HRID 2278869 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH3:18].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C([O-])(=O)C>[NH2:3][C:4]1[N:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[N:10]=[C:9]2[C:5]=1[N:6]=[C:7]([Br:1])[N:8]2[CH3:18]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24408Bromine2×HCID 656671Sodium PyrosulfiteHCID 66671682HCID 66671682, compound

Product 1

HCID 66671626HCID 66671626, compound

Reagents, catalysts & solvents 2

HCID 175AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Bromine (0.4 ml, 6.8 mmol) was added dropwise, at −14° C., to 4-(6-amino-9-methyl-9H-purin-2-yl)butan-1-ol (250 mg, 1.13 mmol) dissolved in a mixture of dioxane (5 ml) and acetate buffer pH 4 (2.5 ml) (obtained by dissolving 4 g of sodium acetate in 100 ml of water and by adjusting to pH 4 with glacial acetic acid). The reaction was stirred at this temperature for 10 minutes and then at RT for 15 minutes. Excess of bromine was eliminated with sodium metabisulphite and the reaction brought to pH 8 by addition of saturated solution of Na2CO3. The aqueous phase was extracted with DCM (6×10). The organic phases were dried over anhydrous sodium sulphate and evaporated under reduced pressure, to give a residue that was used for the following reaction without further purification.

Workup

  1. waitat RT for 15 minutes
  2. extractionThe aqueous phase was extracted with DCM (6×10)
  3. dry with materialThe organic phases were dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure
  5. customto give a residue that
  6. customwas used for the following reaction without further purification

Sources & evidence

ORD record
ord-a94abd10c0fe4decbc4678d2d5447dbe
Source dataset
uspto-grants-2015_09
Patent number
US09133197B2

Reaction notes

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