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2-Methylpentane → 2-Butan-2-yl-10-chloro-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one

HRID 2234393
ノート
印刷プレビュー

反応式

HRID 2234393 の反応式
Br[C:2]1[C:3]([N:9]([CH:16]([CH2:18][CH3:19])[CH3:17])[CH2:10][CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.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.CCCC(C)C>O1CCOCC1.C(Cl)Cl.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]>[CH3:17][CH:16]([N:9]1[CH2:10][CH2:11][C:12](=[O:13])[N:14]([CH3:15])[C:2]2[C:3]1=[N:4][C:5]([Cl:8])=[N:6][CH:7]=2)[CH2:18][CH3:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 78922-MethylpentaneHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866175713-[(5-bromo-2-chloro-pyrimidin-4-yl)-butan-2-yl-amino]-N-methyl-propanamide2 回

生成物 1

HCID 866175702-Butan-2-yl-10-chloro-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-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 solution of 3-[(5-bromo-2-chloro-pyrimidin-4-yl)-butan-2-yl-amino]-N-methyl-propanamide (Intermediate 88; 559 mg, 1.60 mmol) in anhydrous 1,4-dioxane (15 mL) was added Caesium Carbonate (1.04 g, 3.19 mmol). Nitrogen was bubbled through the reaction mixture for 10 minutes, prior to addition of Tris(dibenzylideneacetone)dipalladium(0) (87 mg, 0.095 mmol) and XANTPHOS (88 mg, 0.152 mmol). The reaction was heated to 100° C. and stirred under nitrogen m for 18 hrs. The reaction mixture was cooled and diluted to ˜40 ml with DCM. The reaction mixture was filtered to remove insoluble material, washing filter cake through with DCM. The filtrate was evaporated to give a brown gum which was purified by flash chromatography on silica (40 g cartridge; ISCO companion) eluting with a 25-75% gradient of ethyl acetate in iso-hexane. Product containing fractions were combined and evaporated to give a waxy off white solid which was trituration with hot iso-hexane afforded, on cooling, and collection by suction filtration the title compound as a pale yellow solid (121 mg, 28%)

後処理

  1. customNitrogen was bubbled through the reaction mixture for 10 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe reaction mixture was filtered
  4. customto remove insoluble material
  5. washwashing
  6. filtrationfilter cake through with DCM
  7. customThe filtrate was evaporated
  8. customto give a brown gum which
  9. customwas purified by flash chromatography on silica (40 g cartridge; ISCO companion)
  10. washeluting with a 25-75% gradient of ethyl acetate in iso-hexane
  11. additionProduct containing fractions
  12. customevaporated
  13. customto give a waxy off white solid which
  14. customafforded
  15. temperatureon cooling
  16. customcollection
  17. filtrationby suction filtration the title compound as a pale yellow solid (121 mg, 28%)

出典と根拠

ORDレコード
ord-b7d02f65fb604d72b1f113429edefcc9
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709471B2

反応ノート

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