Sodium Iodide → HCID 59834736, compound

HRID 271617Notes

Reaction equation

HRID 271617 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[C:20](=[O:21])[C:19]2([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[O:18][C:17]1=[O:27].[CH2:30](Br)[CH3:31].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C.O>[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[C:20](=[O:21])[C:19]2([CH2:22][CH2:23][N:24]([CH2:30][CH3:31])[CH2:25][CH2:26]2)[O:18][C:17]1=[O:27]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 59834607HCID 59834607, compound

Product 1

HCID 59834736HCID 59834736, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2,2-dimethyl-propyl)-6-(2,4-dioxo-1-oxa-3,8-diaza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.63 mmol) in DMF (2 ml) are added ethyl bromide (0.69 mmol), K2CO3 (0.76 mmol), and NaI (0.95 mmol). The mixture is allowed to stir at ambient temperature under nitrogen atmosphere for 18 hours. The reaction mixture is diluted with H2O and extracted with AcOEt. The organic layer is washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by HPLC(H2O—0.1% TFA/acetonitrile—0.1% TFA). Fractions are collected, basified with 5% aqueous NaHCO3, extracted with AcOEt, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 7-(2,2-dimethyl-propyl)-6-(8-ethyl-2,4-dioxo-1-oxa-3,8-diaza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by HPLC(H2O—0.1% TFA/acetonitrile—0.1% TFA)
  6. customFractions are collected
  7. extractionextracted with AcOEt
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb95cd88e7f248adbcacc59a02c6a528
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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