N-bromobutanimide → 8-Bromo-2-butoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 558448Notes

Reaction equation

HRID 558448 reaction equation
[CH2:1]([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)[CH2:2][CH2:3][CH3:4].[Br:22]N1C(=O)CCC1=O>C(Cl)Cl>[Br:22][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][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20301001HCID 20301001, compound

Product 1

HCID 231585488-Bromo-2-butoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (ii) (30 g) was dissolved in dry DCM (200 ml). The solution was stirred at rt whilst N-bromosuccinimide (27 g) was added portion wise. The mixture was stirred at rt overnight. 20% (w/v)-Sodium sulfate (200 ml) was added and the separated aqueous phase extracted with DCM. The combined organic phase was washed with saturated NaHCO3 solution and brine. After concentration in vacuo, the residue was dissolved in EtOAc, washed with water, brine and dried. The solution was filtered through silica gel. The filtrate was concentrated in vacuo and dissolved in a mixture of diethyl ether and isohexane (1/1, 200 ml) to give the subtitle compound (26 g). The solvent was removed to give a residue, which was purified by column chromatography (EtOAc/isohexane), which afforded 2.5 g. The solids were combined to give the subtitle compound as a yellow solid. Yield 28.5 g. Melting point: 148-150° C.

Workup

  1. additionwas added portion wise
  2. extractionthe separated aqueous phase extracted with DCM
  3. washThe combined organic phase was washed with saturated NaHCO3 solution and brine
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue was dissolved in EtOAc
  6. washwashed with water, brine
  7. customdried
  8. filtrationThe solution was filtered through silica gel
  9. concentrationThe filtrate was concentrated in vacuo
  10. dissolutiondissolved in a mixture of diethyl ether and isohexane (1/1, 200 ml)

Sources & evidence

ORD record
ord-cf22d8080bdb4f0f9b938d717530cc70
Source dataset
uspto-grants-2011_11
Patent number
US08063051B2

Reaction notes

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