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

HRID 562486Notes

Reaction equation

HRID 562486 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]NC(=O)CCC(N)=O>ClCCl>[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 9834204N-BromosuccinamideHCID 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 dichloromethane (200 ml). The solution was stirred at room temperature whilst N-bromosuccinamide (27 g) was added portionwise. The mixture was stirred at ambient temperature overnight. 20% (w/v)-Sodium sulfate (200 ml) was added and the separated aqueous phase extracted with dichloromethane. The combined organic phase was washed with saturated sodium hydrogen carbonate solution and brine. After concentration in vacuo, the residue was dissolved in ethyl acetate, washed with water, brine and dried. The solution was filtered through silica gel and concentrated in vacuo. The residue was triturated with diethyl ether and isohexane (1/1, 200 ml) then filtered to give the subtitle compound (26 g). The filtrate was concentrated in vacuo and the residue purified by column chromatography (ethyl acetate/isohexane) to give a further 2.5 g of product. The solids were combined to give the subtitle compound as a yellow solid. Yield 28.5 g. mp 148-50° C.

Workup

  1. additionwas added portionwise
  2. extractionthe separated aqueous phase extracted with dichloromethane
  3. washThe combined organic phase was washed with saturated sodium hydrogen carbonate solution and brine
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with water, brine
  7. customdried
  8. filtrationThe solution was filtered through silica gel
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with diethyl ether and isohexane (1/1, 200 ml)
  11. filtrationthen filtered

Sources & evidence

ORD record
ord-f6003dee2b7b4b8a913b67e628674d1b
Source dataset
uspto-grants-2011_11
Patent number
US08067411B2

Reaction notes

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