Triethylamine → 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide

HRID 874511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874511
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][O:6][C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH2:30].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][O:6][C:7]1[C:12]([C:13]([NH:30][CH2:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)=[O:15])=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712350394-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic Acid

Produkt 1

HCID 712351214-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic acid (300 mg, 0.88 mmol) and pyridin-2-ylmethylamine (115 mg, 1.06 mmol) were dissolved in 10 mL of THF, triethylamine (141 mg, 1.4 mmol) was added dropwise, added HATU (405 mg, 1.06 mmol) under ice-water-bath, reacted at room temperature for 4 h, to the reaction solution was added 100 mL of water, then extracted with dichloromethane, dried with anhydrous sodium sulfate, dried by rotation, then the solid was separated with silica gel column (dichloromethane:methanol=20:1) to obtain a white solid 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide 180 mg, yield 48%.

Aufarbeitung

  1. customreacted at room temperature for 4 h, to the reaction solution
  2. extractionextracted with dichloromethane
  3. dry with materialdried with anhydrous sodium sulfate
  4. customdried by rotation
  5. customthe solid was separated with silica gel column (dichloromethane:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-a4b3b7ee9b164790a50d38ef128e0ced
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980904B2

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