N-bromobutanimide → 8-Bromo-N2-(cyclohexylmethyl)-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-Purine-2,6-diamine

HRID 1011011Notes

Reaction equation

HRID 1011011 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][N:15]3[CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:11]([NH2:25])[N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:33])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:33][C:14]1[N:15]([CH2:18][CH:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:16]2[C:12]([N:13]=1)=[C:11]([NH2:25])[N:10]=[C:9]([NH:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[N:17]=2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 57699751N2-(cyclohexylmethyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine-2,6-diamine

Product 1

HCID 576996278-Bromo-N2-(cyclohexylmethyl)-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-Purine-2,6-diamine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N2-(cyclohexylmethyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine-2,6-diamine (90 mg) in dry chloroform (1 mL) at room temperature was added NBS (46 mg) in one go. The dark brown reaction was stirred at RT for 1 hour. The reaction was diluted with DCM (15 mL) and washed with water (5 mL). The organics were passed through a hydrophobic frit and concentrated in vacuo.

Workup

  1. customThe dark brown reaction
  2. washwashed with water (5 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51c8f36c74e944d09ba2ba84f4f27ccd
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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