홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Hydrogen Peroxide → 3-benzyl-2-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1784463
노트
인쇄 미리보기

반응식

HRID 1784463 반응식
[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][N:6]2[C:7](=[O:10])[C:8]=1I.[O-]P([O-])([O-])=O.[K+].[K+].[K+].B1([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)C2CCCC1CCC2.[OH-].[Na+].OO>CN(C=O)C.C(OCC)(=O)C.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH2:32]([C:8]1[C:7](=[O:10])[N:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]2=[N:4][C:3]=1[CH2:2][OH:1])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 596541742-(Hydroxymethyl)-3-iodo-4h-pyrido[1,2-a]pyrimidin-4-one

생성물 1

HCID 596541663-benzyl-2-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one
수율 91%

시약·촉매·용매 3

HCID 53485975CID 53485975촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매5회

반응 조건

온도
80 °C

실험 절차

A mixture of 4.0 g (13.24 mmol) of the product from Step 4 (14), 1.0 g (1.32 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene] palladium(II) dichloromethane adduct, and 8.4 g (39.72 mmol) of K3PO4 in 30 mL of DMF was heated to 80° C. To the resulting solution was added dropwise 40 mL (19.9 mmol) of B-Benzyl-9-BBN and stirred at 80° C. under nitrogen for 12 hours. The reaction was then cooled to 0° C. and excess 1N NaOH was added to the reaction mixture. Excess 30% H2O2 was then added to the mixture at 0° C. resulting in significant gas evolution. Stirring continued for at least one additional hour or until gas ceased to evolve. The mixture was extracted with ethyl acetate (3×) and washed with saturated Na2O3S2 and brine. The organic layers were combined, dried over MgSO4 and activated carbon, and the solvent was removed in vacuo. The resulting material was subjected to flash chromatography on a 10 cm column. Elution with a gradient of 100% hexanes, 20% ethyl acetate in hexanes, 33% ethyl acetate in hexanes, 43% ethyl acetate in hexanes, 50% ethyl acetate in hexanes, 57% ethyl acetate in hexanes, 67% ethyl acetate in hexanes, and 100% ethyl acetate yielded 3.2 g (12.0 mmol, 91%) of 3-benzyl-2-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (15) as a pale yellow solid.

후처리

  1. temperatureThe reaction was then cooled to 0° C.
  2. customresulting in significant gas evolution
  3. stirringStirring
  4. extractionThe mixture was extracted with ethyl acetate (3×)
  5. washwashed with saturated Na2O3S2 and brine
  6. dry with materialdried over MgSO4 and activated carbon
  7. customthe solvent was removed in vacuo
  8. washElution with a gradient of 100% hexanes, 20% ethyl acetate in hexanes, 33% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-465f2de5c44f4eafb490bd0a27c9b5c6
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07504405B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트