Acetate → HCID 66776742, compound

HRID 2278878Notes

Reaction equation

HRID 2278878 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:12]=[C:11]([CH:13]([OH:17])[CH2:14][CH2:15][CH3:16])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH3:18].C([O-])(=O)C.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>CO.C1COCC1>[NH2:3][C:4]1[N:12]=[C:11]([CH:13]([OH:17])[CH2:14][CH2:15][CH3:16])[N:10]=[C:9]2[C:5]=1[N:6]=[C:7]([Br:1])[N:8]2[CH3:18]

Participants

8

Reactant 5

HCID 175AcetateHCID 10340Sodium CarbonateHCID 24408Bromine2×HCID 656671Sodium PyrosulfiteHCID 66777001HCID 66777001, compound

Product 1

HCID 66776742HCID 66776742, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Bromine (3.6 ml, 70.4 mmol) was added dropwise, at −14° C., to 1-(6-amino-9-methyl-9H-purin-2-yl)butan-1-ol (1700 mg, 7.69 mmol) dissolved in a mixture of MeOH (20 ml), THF (20 ml) and acetate buffer pH 4 (20 ml) (obtained by dissolving 4 g of sodium acetate in 100 ml of water and by adjusting pH 4 with glacial acetic acid). The reaction was stirred at this temperature for 15 minutes and then at RT for 10 minutes. Excess of bromine was eliminated with sodium metabisulphite and the reaction brought to pH 8 by addition of saturated solution of Na2CO3. The organic solvents were evaporated under reduced pressure, to give a solid that was filtered and used for the following reaction without further purification.

Workup

  1. waitat RT for 10 minutes
  2. customThe organic solvents were evaporated under reduced pressure
  3. customto give a solid
  4. filtrationthat was filtered
  5. customused for the following reaction without further purification

Sources & evidence

ORD record
ord-03d5781878d1409fa910bdc3310bb056
Source dataset
uspto-grants-2015_09
Patent number
US09133197B2

Reaction notes

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