Triethylamine → HCID 59834684, compound

HRID 271580Notes

Reaction equation

HRID 271580 reaction equation
Br[C:2]1[C:3]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH2:16]([N:19]1[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]1)[C:17]#[CH:18].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:13][C:12]([CH3:15])([CH3:14])[CH2:11][N:10]1[C:3]2[N:4]=[C:5]([C:8]#[N:9])[N:6]=[CH:7][C:2]=2[CH:18]=[C:17]1[CH2:16][N:19]1[CH2:20][CH2:21][S:22](=[O:25])(=[O:26])[CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27772654-(Prop-2-yn-1-yl)-1lambda~6~,4-thiazinane-1,1-dioneHCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrile

Product 1

HCID 59834684HCID 59834684, compoundYield 1.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.54 g (2 mmoles) of 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile and 0.75 g (4.3 mmoles) of 4-propargylthiomorpholine-1,1-dioxide in 5 ml of DMF are added 0.841 ml (6 mmoles) of triethylamine, 0.38 g (2 mmoles) of copper(I) iodide and 0.14 g (0.2 mmoles) of Pd(PPh3)2Cl2under nitrogen atmosphere. The mixture is stirred for 31 hours at 80° C. The mixture is filtered through celite, diluted with AcOEt, washed with H2O and brine, dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by HPLC(H2O—0.1% TFA/CH3CN—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. The resulting residue is then purified by HPLC (n-Hexane/AcOEt) to give 0.01 g of desired 7-(2,2-dimethyl-propyl)-6-(1,1-dioxo-1λ6-thiomorpholin-4-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 1.4% yield.

Workup

  1. filtrationThe mixture is filtered through celite
  2. additiondiluted with AcOEt
  3. washwashed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by HPLC(H2O—0.1% TFA/CH3CN—0.1% TFA)
  7. customFractions are collected
  8. extractionextracted with AcOEt
  9. washwashed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting residue is then purified by HPLC (n-Hexane/AcOEt)

Sources & evidence

ORD record
ord-a4c34d7b0a504c5eaac4676a75a7fbc2
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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