Cesium carbonate → HCID 59526288、化合物

HRID 386112

反応式

HRID 386112 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 59526288HCID 59526288、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e19c56592412448cb3a2c0c46f28c929
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

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