Acetate → HCID 66671727, compound

HRID 2278881Notes

Reaction equation

HRID 2278881 reaction equation
[Br:1]Br.[CH2:3]([N:10]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:11]1[N:19]=[C:18]([CH2:20][CH2:21][C:22]2([CH3:30])[O:27][CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][O:23]2)[N:17]=[C:16]2[C:12]=1[N:13]=[CH:14][N:15]2[CH3:31])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.C([O-])(=O)C.[Na+]>O.C(O)(=O)C.CO.C1COCC1>[CH2:3]([N:10]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:11]1[N:19]=[C:18]([CH2:20][CH2:21][C:22]2([CH3:30])[O:23][CH2:24][C:25]([CH3:29])([CH3:28])[CH2:26][O:27]2)[N:17]=[C:16]2[C:12]=1[N:13]=[C:14]([Br:1])[N:15]2[CH3:31])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 175AcetateHCID 24408BromineHCID 517045Sodium AcetateHCID 66671498HCID 66671498, compound

Product 1

HCID 66671727HCID 66671727, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Bromine (0.89 ml, 17.5 mmol) was added dropwise at 0° C. to a solution of dibenzyl-{9-methyl-2-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-9H-purin-6-yl}-amine (1.7 g, 3.50 mmol) in 20 ml of a mixture of MeOH/THF (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 RT for two hours. 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 in the next step.

Workup

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

Sources & evidence

ORD record
ord-9ca93fa66ae0495ab8855d14b1fa6e08
Source dataset
uspto-grants-2015_09
Patent number
US09133197B2

Reaction notes

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