1,2-Dibromoethane → 7-(2-bromoethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 639484Notes

Reaction equation

HRID 639484 reaction equation
[Cl:1][C:2]1[C:3]2[CH:11]=[CH:10][NH:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.[Br:12][CH2:13][CH2:14]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Br:12][CH2:13][CH2:14][N:9]1[C:4]2[N:5]=[C:6]([NH2:8])[N:7]=[C:2]([Cl:1])[C:3]=2[CH:11]=[CH:10]1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 53244134-chloro-7H-pyrrolo(2,3-d)pyrimidin-2-amine

Product 1

HCID 866234677-(2-bromoethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (170 mg, 1.01 mmol), 1,2-dibromoethane (0.70 mL, 8.08 mmol), and tetra-n-butylammonium bromide (20 mg) are dissolved in THF (4 mL), and 30% aqueous NaOH (1.01 mL, 7.58 mmol) is added. The mixture is stirred for 24 h at RT, then partitioned between water and EtOAc. The aqueous solution is extracted with additional EtOAc, and the combined organic layers are dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated to dryness. The residue is purified by column chromatography on silica gel, eluting with 2:1-DCM:EtOAc. Fractions containing product are combined and evaporated to dryness to provide 7-(2-bromoethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine as a yellow solid: LC/MS (M+1=276.9). 1H NMR (CDCl3) δ 3.66 (t, 2H, J=8.0 Hz), 4.44 (t, 2H, J=8.0 Hz), 4.92 (br s, 2H), 6.39 (d, 1H, J=4.0 Hz), 6.92 (d, 1H, J=4.0 Hz).

Workup

  1. custompartitioned between water and EtOAc
  2. extractionThe aqueous solution is extracted with additional EtOAc
  3. dry with materialthe combined organic layers are dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue is purified by column chromatography on silica gel
  7. washeluting with 2
  8. additionFractions containing product
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-c2ce70339d0e44108e18da75f29af51a
Source dataset
uspto-grants-2010_04
Patent number
US07691869B2

Reaction notes

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