N-Iodosuccinimide → HCID 69215330, compound

HRID 900167Notes

Reaction equation

HRID 900167 reaction equation
[C:1]1([C:7]2[C:15]3[C:14]([NH:16][CH2:17][C@@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)=[N:13][CH:12]=[N:11][C:10]=3[NH:9][C:8]=2[Si](CC)(CC)CC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:30]N1C(=O)CCC1=O>CN(C=O)C>[I:30][C:8]1[NH:9][C:10]2[N:11]=[CH:12][N:13]=[C:14]([NH:16][CH2:17][C@@H:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[C:15]=2[C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 71470591HCID 71470591, compound

Product 1

HCID 69215330HCID 69215330, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.00 g (2.5 mmol) of (S)-[5-phenyl-6-(triethylsilanyl)-7-H-pyrrolo[2,3-d]pyrimidine-4-yl]-(tetrahydrofuran-2-ylmethyl)-amine and 830 mg (3.7 mmol) of N-iodosuccinimide in 10 ml DMF was stirred at 45° C. for 1 h. The reaction mixture was partitioned between dichloromethane (120 ml) and a 4:1 mixture of brine and saturated aqueous sodium thiosulfate (35 ml). The organic layer was washed with saturated aqueous sodium bicarbonate (1×) and brine (1×), dried over Na2SO4, filtered and concentrated. The residue was dissolved in dichloromethane (10 ml), and hexanes (200 ml) was added slowly. A solid precipitate formed. The solid was filtered off and dried under high vacuum to give the title compound. 1H-NMR (400 MHz, CDCl3) δ 1.51 (m, 1 H), 1.69-1.91 (m, 3 H), 3.19-3.69 (m, 4 H), 3.99 (m, 1 H), 5.27 (t, J=4.4 Hz, 1 H), 7.37-7.56 (m, 5 H), 8.42 (s, 1 H), 13.21 (s, 1 H). Mass Spectrum (ESI) m/e=421.0 (M+1).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (120 ml)
  2. additiona 4:1 mixture of brine and saturated aqueous sodium thiosulfate (35 ml)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate (1×) and brine (1×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  8. additionhexanes (200 ml) was added slowly
  9. customA solid precipitate formed
  10. filtrationThe solid was filtered off
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-e101fc91eae14522b680aacc584163b3
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

Loading…