Acetic Anhydride → 2-(Acetylamino)-3,6-dihydro-4-methyl-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid, diethyl ester

HRID 1789580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789580
[NH2:1][C:2]1[N:3]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[C:28]([NH:1][CH:2]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[N:3]1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:30])[CH3:29]

Komponenten

6

Edukt 2

HCID 7918Acetic AnhydrideHCID 139572692-Amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester

Produkt 1

HCID 139572712-(Acetylamino)-3,6-dihydro-4-methyl-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid, diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (550 mg, 1.46 mmoles, see Example 2) in dichloromethane (5.0 ml) and pyridine (0.5 ml) was treated with acetic anhydride (0.3 ml) and the reaction was allowed to stir at room temperature for 1 hour. The colorless reaction mixture was diluted with ethyl acetate and was washed with 5% citric acid, sodium bicarbonate solution and brine. It was dried over anhydrous magnesium sulfate and evaporated to provide a colorless foam. Crystallization from ether-hexanes provided the title compound as a colorless solid, melting point 154.5°-156° C.

Aufarbeitung

  1. washwas washed with 5% citric acid, sodium bicarbonate solution and brine
  2. dry with materialIt was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customto provide a colorless foam
  5. customCrystallization from ether-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-99317e12e9e34e248ca2fd650b9d5d3c
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689414

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