Cesium carbonate → 5-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one

HRID 1918822ノート

反応式

HRID 1918822 の反応式
[CH:1]1([N:4]2[CH:8]=[C:7]([NH2:9])[CH:6]=[N:5]2)[CH2:3][CH2:2]1.Br[C:11]1[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=[C:15]([Br:17])[N:16]=1.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.C([O-])([O-])=O.[Cs+].[Cs+]>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].C(Cl)Cl.O1CCOCC1>[Br:17][C:15]1[N:16]=[C:11]([NH:9][C:7]2[CH:6]=[N:5][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH:8]=2)[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 510003781-Cyclopropyl-1H-pyrazol-4-amine

生成物 1

HCID 580442185-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a seal tube equipped with a stirring bar, 1-cyclopropyl-1H-pyrazol-4-amine (600 mg, 4.87 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (1.96 g, 7.31 mmol), Pd2(dba)3 (223.1 mg, 0.244 mmol), XantPhos (225.5 mg, 0.390 mmol), Cs2CO3 (5.25 g, 16.08 mmol) and dioxane (12 mL) were added. The tube was sealed and heated at 100° C. overnight. CH2Cl2 (200 mL) was added to the resulting mixture, and the CH2Cl2 solution was washed with water (30 mL×3). The precipitate in the aqueous phase was filtered as pure product 114b. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo. CH2Cl2/ether (1:2, 3 mL) were added to the residue and the mixture was sonicated. The precipitate was filtered, combined with the filtered solids from the aqueous phase, and dried. 5-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one 114b was obtained as a yellow solid.

後処理

  1. customTo a seal tube equipped with a stirring bar
  2. customThe tube was sealed
  3. washthe CH2Cl2 solution was washed with water (30 mL×3)
  4. filtrationThe precipitate in the aqueous phase was filtered as pure product 114b
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. additionCH2Cl2/ether (1:2, 3 mL) were added to the residue
  9. customthe mixture was sonicated
  10. filtrationThe precipitate was filtered
  11. customdried

出典と根拠

ORDレコード
ord-fcbd57cb81a241cab9dd60b564ffe735
出典データセット
uspto-grants-2013_12
特許番号
US08618107B2

反応ノート

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