N-bromobutanimide → 8-Bromo-2-{[1-methyl-2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amine

HRID 1011005Notes

Reaction equation

HRID 1011005 reaction equation
[CH3:1][CH:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[C:9]([NH2:22])[N:8]=1)[CH2:3][O:4][CH3:5].C1C(=O)N([Br:30])C(=O)C1>ClCCl>[Br:30][C:12]1[N:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:14]2[C:10]([N:11]=1)=[C:9]([NH2:22])[N:8]=[C:7]([O:6][CH:2]([CH3:1])[CH2:3][O:4][CH3:5])[N:15]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 576996342-{[1-Methyl-2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576996558-Bromo-2-{[1-methyl-2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amineYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-{[1-methyl-2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (7.2 g, 23.4 mmol) in dichloromethane (100 ml) was added NBS (4.6 g, 25.8 mmol). After 4 h, the solvent was removed. The product was purified on a silica column using petroleum ether: ethyl acetate 2:1 as eluent. This gave the product (7.3 g, 81.1%).

Workup

  1. customthe solvent was removed
  2. customThe product was purified on a silica column

Sources & evidence

ORD record
ord-050983c4f02c4d579363bfdb0b5e0434
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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