3-Amino-4-methoxybenzamide → HCID 86633974, Verbindung

HRID 1041248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041248
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH2:7])=[O:6].[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([Cl:21])=[CH:16][N:15]=1>O1CCCC1>[Cl:13][C:14]1[N:19]=[C:18]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[O:11][CH3:12])[C:5]([NH2:7])=[O:6])[C:17]([Cl:21])=[CH:16][N:15]=1

Komponenten

4

Edukt 2

HCID 871353-Amino-4-methoxybenzamideHCID 2372592,4,5-Trichloropyrimidine

Produkt 1

HCID 86633974HCID 86633974, VerbindungAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Amino-4-methoxy-benzamide (1.00 g, 0.00602 mol) in tetrahydrofuran (40 mL) was treated with 2,4,5-trichloro-pyrimidine (0.8278 mL, 0.007221 mol), and the reaction was stirred overnight at room temperature, then for 4 hours at 50° C. The mixture was partitioned between water and dichloromethane, and the aqueous phase was extracted twice with dichloromethane. The organics were dried (MgSO4) and concentrated, and the product was isolated by chromatography (Silica, MeOH/dichloromethane 0-3%), followed by crystallization from methanol to give 3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methoxy-benzamide as a white solid (1.26 g, 64%). LC/MS (ESI+): 313.04 (M+H).

Aufarbeitung

  1. waitfor 4 hours at 50° C
  2. customThe mixture was partitioned between water and dichloromethane
  3. extractionthe aqueous phase was extracted twice with dichloromethane
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe product was isolated by chromatography (Silica, MeOH/dichloromethane 0-3%)
  7. customfollowed by crystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-180297a366f04fa8867061fcae7221ad
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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