Acetic Acid → HCID 66777068, compound

HRID 2278874Notes

Reaction equation

HRID 2278874 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:12]=[C:11]([CH2:13][CH2:14][CH:15]([OH:17])[CH3:16])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH3:18].C([O-])(=O)C.[Na+].C(O)(=O)C>CO.C1COCC1.C([O-])(=O)C.O>[NH2:3][C:4]1[N:12]=[C:11]([CH2:13][CH2:14][CH:15]([OH:17])[CH3:16])[N:10]=[C:9]2[C:5]=1[N:6]=[C:7]([Br:1])[N:8]2[CH3:18]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 66671496HCID 66671496, compound

Product 1

HCID 66777068HCID 66777068, compound

Reagents, catalysts & solvents 3

HCID 175AcetateSolventHCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Bromine (2.1 ml, 41 mmol) was added dropwise at −14° C. to a solution of 4-(6-amino-9-methyl-9H-purin-2-yl)butan-2-ol (800 mg, 3.60 mmol) in a mixture of MeOH/THF (20 ml, 1/1) and acetate buffer pH=4 (10 ml). The latter was obtained dissolving 4 g of sodium acetate in 100 ml of water and by adjusting to pH 4 through addition of glacial acetic acid. The reaction was stirred at this temperature for 10 minutes and then at RT for 10 minutes. Excess of bromine was quenched by addition of sodium metabisulphite and the reaction was brought to pH 8 by addition of a saturated solution of Na2CO3. The organic solvents were evaporated under reduced pressure, to give a solid that was filtered and used without any further purification.

Workup

  1. customThe latter was obtained
  2. waitat RT for 10 minutes
  3. customExcess of bromine was quenched by addition of sodium metabisulphite
  4. additionthe reaction was brought to pH 8 by addition of a saturated solution of Na2CO3
  5. customThe organic solvents were evaporated under reduced pressure
  6. customto give a solid
  7. filtrationthat was filtered
  8. customused without any further purification

Sources & evidence

ORD record
ord-815e9891252a4583be99151e67c693d7
Source dataset
uspto-grants-2015_09
Patent number
US09133197B2

Reaction notes

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