Dichloromethane → 8-Bromo-2-[(3-methylbutyl)oxy]-9-(tetrahydro-2H-Pyran-2-yl)-9H-Purin-6-amine

HRID 1010957Notes

Reaction equation

HRID 1010957 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[C:8]([NH2:21])[N:7]=1.C1C(=O)N([Br:30])C(=O)C1.C(Cl)Cl>C(Cl)(Cl)Cl>[Br:30][C:11]1[N:12]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:13]2[C:9]([N:10]=1)=[C:8]([NH2:21])[N:7]=[C:6]([O:5][CH2:4][CH2:3][CH:2]([CH3:22])[CH3:1])[N:14]=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 576995832-[(3-Methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-Purin-6-amine

Product 1

HCID 576996758-Bromo-2-[(3-methylbutyl)oxy]-9-(tetrahydro-2H-Pyran-2-yl)-9H-Purin-6-amineYield 93.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-[(3-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (266 mg) in dry chloroform (3.15 mL) at 0° C. was added NBS (163 mg). The reaction was warmed to room temperature and was stirred for 5 h. The reaction was taken up into DCM (20 mL) and extracted with water (20 mL). The organics were separated, dried using a hydrophobic frit and concentrated in vacuo to give the title compound as a green/brown solid (314 mg).

Workup

  1. extractionextracted with water (20 mL)
  2. customThe organics were separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1d24b363a7849cdbeea3efb079beb5a
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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