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

Triethylamine → 5-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-3-benzyl-2-(4-fluorophenylamino)pyrimidin-4(3H)-one

HRID 2246477
노트
인쇄 미리보기

반응식

HRID 2246477 반응식
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([F:22])[CH:16]=2)=[CH:11][N:10]=[C:9]1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:32]1[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[CH:33]=1.CCN(CC)CC>CN1C(=O)CCC1.CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH2:38][C:34]1[CH:33]=[C:32]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:12]3[C:13](=[O:14])[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:9]([NH:23][C:24]4[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=4)=[N:10][CH:11]=3)=[CH:16][C:17]=2[F:22])[CH:37]=[CH:36][N:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8471Triethylamine2회HCID 5818662-Amino-4-chloropyridine2회HCID 592183623-benzyl-5-(3-fluoro-4-hydroxyphenyl)-2-(4-fluorophenylamino)pyrimidin-4(3H)-one

생성물 1

HCID 592183715-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-3-benzyl-2-(4-fluorophenylamino)pyrimidin-4(3H)-one

시약·촉매·용매 3

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매
HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

3-benzyl-5-(3-fluoro-4-hydroxyphenyl)-2-(4-fluorophenylamino)pyrimidin-4(3H)-one (731.4 mg, 1.804 mmol) and 4-chloropyridin-2-amine (473.7 mg, 3.685 mmol) were dissolved in NMP (8.0 ml) and Et3N (1.25 ml, 8.97 mmol) was added. The flask was fitted with a reflux condenser and placed in a preheated oil bath (190 C) and stirred under nitrogen. After 19 hours, more 4-chloropyridin-2-amine (409 mg, 3.20 mmol), DMAP (286.5 mg, 2.345 mmol), Et3N (0.50 ml, 3.6 mmol) were added, followed by NMP (1.0 ml). Stirring was continued at 190 C. After 23 hours, the reaction was cooled to room temperature, diluted with DCM, and washed with water (2×50 ml). The aqueous extracts were combined and extracted with DCM. Some MeOH (˜10%) was also used to help solubilize the biphasic mixture. All the organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on silica gel (˜3 inches, DCM->50:1->20:1 DCM/MeOH) to afford the desired 5-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-3-benzyl-2-(4-fluorophenylamino)pyrimidin-4(3H)-one, which was taken on to the next step. MS (ESI pos. ion) m/z: 498 (MH+). Calc'd exact mass for C28H21F2N5O2: 497.

후처리

  1. customThe flask was fitted with a reflux condenser
  2. customplaced in a preheated oil bath
  3. stirringStirring
  4. waitAfter 23 hours
  5. washwashed with water (2×50 ml)
  6. extractionextracted with DCM
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on silica gel (˜3 inches, DCM->50:1->20:1 DCM/MeOH)

출처 및 근거

ORD 기록
ord-54a829225d204537a7fc3cf2af07f9f6
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07687522B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트