1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 2-(4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

HRID 657728

反応式

HRID 657728 の反応式
[CH3:1][O:2][C:3]1[C:4]2[CH2:12][NH:11][CH2:10][CH2:9][C:5]=2[N:6]=[CH:7][N:8]=1.Br[C:14]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:15]=1[C:16]#[N:17].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.CC(C)([O-])C.[Na+]>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]>[CH3:1][O:2][C:3]1[C:4]2[CH2:12][N:11]([C:14]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:15]=3[C:16]#[N:17])[CH2:10][CH2:9][C:5]=2[N:6]=[CH:7][N:8]=1

参加物

6

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 125572012-Bromo-5-methylbenzonitrileHCID 23676156Sodium t-butoxideHCID 509892144-methoxy-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine

生成物 1

HCID 598407122-(4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

試薬・触媒・溶媒 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒

実験手順

A 100 mL flask was charged with 4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.78 g, 16 mmol), 2-bromo-5-methylbenzonitrile (4.18 g, 19.2 mmol), bis(dibenzylideneacetone)palladium(0) (372 mg, 0.64 mmol), xantphos (529 mg, 0.896 mmol), and sodium tert-butoxide (2.33 g, 24 mmol), capped with a septum and purged with nitrogen. Dry argon-sparged toluene (50 mL) was added. The heterogeneous mixture was placed in an oil bath at 100° C., and heated under argon overnight. After 14 hours, TLC showed the reaction was complete. The mixture was removed from the heat, diluted with ethyl acetate (50 mL), filtered and concentrated in vacuo. The residue was purified by silica gel column (0-100% EtOAc/hexane) to afford a light orange solid.

後処理

  1. customcapped with a septum
  2. custompurged with nitrogen
  3. customDry argon-sparged toluene (50 mL)
  4. additionwas added
  5. customThe heterogeneous mixture was placed in an oil bath at 100° C.
  6. temperatureheated under argon overnight
  7. customThe mixture was removed from the heat
  8. additiondiluted with ethyl acetate (50 mL)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column (0-100% EtOAc/hexane)
  12. customto afford a light orange solid

出典と根拠

ORDレコード
ord-21cd55d605a647a0bbd887eacb573e8f
出典データセット
uspto-grants-2011_12
特許番号
US08076345B2

関連ノート

読み込み中…