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

HRID 2246477
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Reaktionsgleichung

Reaktionsgleichung von HRID 2246477
[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
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Komponenten

7

Edukt 3

HCID 8471Triethylamine2×HCID 5818662-Amino-4-chloropyridine2×HCID 592183623-benzyl-5-(3-fluoro-4-hydroxyphenyl)-2-(4-fluorophenylamino)pyrimidin-4(3H)-one

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-54a829225d204537a7fc3cf2af07f9f6
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07687522B2

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