N-bromobutanimide → 8-Bromo-2-chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

HRID 1010974Notes

Reaction equation

HRID 1010974 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([NH2:18])[N:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:26][C:7]1[N:8]([CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:5]([N:6]=1)=[C:4]([NH2:18])[N:3]=[C:2]([Cl:1])[N:10]=2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 576998042-Chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

Product 1

HCID 576996638-Bromo-2-chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amineYield 80.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (1.30 g) in dry chloroform (32 mL) at room temperature was added NBS (2.16 g). The reaction was stirred at 60° C. for 6 h. the mixture was cooled, taken up in DCM (50 mL) and washed with water (50 mL). The organics were passed through a hydrophobic frit and concentrated in vacuo to give the title compound as a brown solid (1.36 g).

Workup

  1. temperaturewas cooled
  2. washwashed with water (50 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-847f75b476864f3991684513d8273bde
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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