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

Sodium Carbonate → 4-Chloro-5-cyclopropyl-2,6-dimethoxy-pyrimidine

HRID 426251
노트
인쇄 미리보기

반응식

HRID 426251 반응식
Br[C:2]1[C:3]([Cl:12])=[N:4][C:5]([O:10][CH3:11])=[N:6][C:7]=1[O:8][CH3:9].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.ClCl.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C(OCC)(=O)C.COCCOC>[Cl:12][C:3]1[C:2]([CH:13]2[CH2:15][CH2:14]2)=[C:7]([O:8][CH3:9])[N:6]=[C:5]([O:10][CH3:11])[N:4]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 24526ChlorineHCID 2760897Cyclopropylboronic acidHCID 122261955-Bromo-4-chloro-2,6-dimethoxypyrimidine

생성물 1

HCID 591847574-Chloro-5-cyclopropyl-2,6-dimethoxy-pyrimidine수율 65.2%

시약·촉매·용매 4

HCID 23938Palladium
촉매
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

In a 5 mL microwave reaction tube, 5-bromo-4-chloro-2,6-dimethoxy-pyrimidine (116 mg, 0.457 mmol), cyclopropyl boronic acid (47 mg, 0.549 mmol, 1.2 eq.) and Pd(dppf(Cl2 (38 mg, 0.1 eq.) was charged with DME (2.5 mL) and 2M Na2CO3 aqueous solution (0.91 mL, 4 eq.). The reaction was heated at 130° C. in the microwave reactor for 30 minutes. Ethyl acetate was added, followed by washing with brine. The organic layer was concentrated down and purified (silica gel, 0-50% EtOAC/hexane) to give white solid (64 mg, 65%). LC-MS shows 215.1 (M+1). 1H NMR (300 MHz, CDCl3): δ 3.98 (dd, 6H), 1.62 (m, 1H), 0.99 (m, 2H), 0.78 (m, 2H).

후처리

  1. washby washing with brine
  2. concentrationThe organic layer was concentrated down
  3. custompurified (silica gel, 0-50% EtOAC/hexane)

출처 및 근거

ORD 기록
ord-c5ba8d2c36214879b6a22c42ec5498a5
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106064B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트