Triethylamine → N-(2-aminopyrimidin-5-yl)-2-methyl-5-nitrobenzamide

HRID 2355072

Reaktionsgleichung

Reaktionsgleichung von HRID 2355072
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[N:14]1[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16][C:15]=1[NH2:21].CCN(CC)CC>O=S(Cl)Cl>[NH2:21][C:15]1[N:16]=[CH:17][C:18]([NH:20][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=2[CH3:1])=[CH:19][N:14]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 229075Pyrimidine-2,5-diamineHCID 5196832-Methyl-5-nitrobenzoic acid

Produkt 1

HCID 16118604N-(2-aminopyrimidin-5-yl)-2-methyl-5-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

2-methyl-5-nitrobenzoic acid (659 mg, 3.64 mmol) was heated to reflux in SOCl2 (6 mL) for 1 h. After cooling to room temperature and concentrating to dryness, the crude acid chloride was taken up in CH2Cl2 (25 mL). Pyrimidine-2,5-diamine 7 (400 mg, 3.64 mmol) was added to the solution and the mixture was allowed to stir at rt over night. The mixture became a thick white suspension. NEt3 (700 □L, 4.73 mmol) was added. After 2 h, a thick-white suspension remained. The mixture was filtered through a Buchner funnel and washed with copious amounts of CH2Cl2 to remove NEt3HCl salt, affording N-(2-aminopyrimidin-5-yl)-2-methyl-5-nitrobenzamide 8 as an off-white solid.

Aufarbeitung

  1. concentrationconcentrating to dryness
  2. filtrationThe mixture was filtered through a Buchner funnel
  3. washwashed with copious amounts of CH2Cl2
  4. customto remove NEt3HCl salt

Quellen und Nachweise

ORD-Eintrag
ord-ee83b56ae6cb45978238754527a7527c
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754717B2

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