Nitric Acid → 2,4-Diamino-5-(3-amino-4-chloro-5-nitrophenyl)-6-ethylpyrimidine

HRID 440942

Reaktionsgleichung

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[C:4]([CH2:16][CH3:17])[N:3]=1.[N+:18]([O-])([OH:20])=[O:19].S(=O)(=O)(O)O>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=2)=[C:4]([CH2:16][CH3:17])[N:3]=1

Komponenten

Edukt 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 4993Pyrimethamine

Produkt 1

HCID 3274042,4-Diamino-5-(3-amino-4-chloro-5-nitrophenyl)-6-ethylpyrimidine

Versuchsvorschrift

In this method, commercially available 2,4-diamino-6-ethyl-5-(4-chlorophenyl)pyrimidine is nitrated with 70% nitric acid and concentrated sulfuric acid, yielding the corresponding 2,4-diamino-6-ethyl-5-(4-chloro-3-nitrophenyl)pyrimidine. The thus-prepared nitrophenylpyrimidine is in turn reduced with stannous chloride dihydrate in 10M hydrochloric acid, yielding the corresponding 2,4-diamino-6-ethyl-5-(3-amino-4-chlorophenyl)pyrimidine. The aminophenylpyrimidine may then be treated with an appropriate acid chloride in the presence of a base in tetrahydrofuran, yielding the desired 2,4-diamino-6-ethyl-5-[3-(substituted-carbonylamino)-4-chlorophenyl]pyrimidine (wherein W is --NHC(O)R4). These compounds may optionally be reduced with 1M boron-tetrahydrofuran complex in tetrahydrofuran, affording 2,4-diamino-6-ethyl-5-[3-(substituted-amino )-4-chlorophenyl]pyrimidine (wherein W is --NHR5).

Quellen und Nachweise

ORD-Eintrag: ord-e7bd41a7e5da4d00ab972fb83c7e27d5
Quelldatensatz: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05521192

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