Cesium carbonate → N'-(4-bromopyrimidin-2-yl)-N,N-dimethylsulfamide

HRID 386112Notes

Reaction equation

HRID 386112 reaction equation
Br[C:2]1[N:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]([CH3:15])[S:11]([NH2:14])(=[O:13])=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:14][S:11]([N:10]([CH3:15])[CH3:9])(=[O:13])=[O:12])[N:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 134472N,N-DimethylsulfamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 149763012,4-Dibromopyrimidine

Product 1

HCID 59526288N'-(4-bromopyrimidin-2-yl)-N,N-dimethylsulfamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Dibromopyrimidine (0.50 g, 2.11 mmol), N,N-dimethylsulfamide (0.26 mg, 2.11 mmol), cesium carbonate (2.75 g, 8.44 mmol), Pd2(dba)3 (0.10 mg, 0.11 mmol), and Xantphos (0.18 mg, 0.32 mmol) were placed in a flask. Dioxane (24 mL) was added and argon was bubbled through the solution for several minutes. The reaction was then heated at 100° C. overnight. The reaction was cooled to ambient temperature, diluted with ethyl acetate, washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated. Reverse phase HPLC was used for purification to yield the title compound.

Workup

  1. customargon was bubbled through the solution for several minutes
  2. temperatureThe reaction was cooled to ambient temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customReverse phase HPLC was used for purification

Sources & evidence

ORD record
ord-e19c56592412448cb3a2c0c46f28c929
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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