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N-bromobutanimide → 8-Bromo-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amine

HRID 1011030
Notes
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Reaction equation

HRID 1011030 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:10]([NH2:23])[N:9]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:24][C:13]1[N:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:15]2[C:11]([N:12]=1)=[C:10]([NH2:23])[N:9]=[C:8]([O:7][CH2:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[N:16]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 576996072-[(Tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576996528-Bromo-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
1 °C

Procedure

2-[(Tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.7202 g) was dissolved in chloroform (15 mL) and cooled to ˜1° C. before N-bromosuccinimide (1.056 g) was added keeping the reaction temperature below 2° C. The reaction mixture was then stirred at ˜1° C. for 30 minutes before allowing to warm to room temperature were upon the reaction mixture was stirred for 3 hours. The reaction mixture was then stood overnight at room temperature before being partitioned between water (50 mL) and the organic phase separated using a hydrophobic frit. The organic phase was evaporated under reduced pressure to give a brown gum which was purified using silica chromatography (ISCO) eluting with 0-100% ethyl acetate: cyclohexane. This gave the title compound as a white foam solid (1.3748 g).

Workup

  1. additionwas added
  2. customthe reaction temperature below 2° C
  3. temperatureto warm to room temperature
  4. stirringwas stirred for 3 hours
  5. waitThe reaction mixture was then stood overnight at room temperature
  6. custombefore being partitioned between water (50 mL)
  7. customthe organic phase separated
  8. customThe organic phase was evaporated under reduced pressure
  9. customto give a brown gum which
  10. customwas purified
  11. washeluting with 0-100% ethyl acetate

Sources & evidence

ORD record
ord-acb95e2d63334859858c8f37aed83801
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977344B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes