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

반응식

HRID 657728 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-21cd55d605a647a0bbd887eacb573e8f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076345B2

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