2,4-Dichloro-5-nitropyrimidine → HCID 19021679, compound

HRID 1108978Notes

Reaction equation

HRID 1108978 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][C:13](C)([O-])C.[Li+].C([Mg]Br)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH2:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 5212662,4-Dichloro-5-nitropyrimidineHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 178418443HCID 178418443, compound

Product 1

HCID 19021679HCID 19021679, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In Scheme A, reaction of 2,4-dichloro-5-nitropyrimidine (1) with lithium t-butoxide, cuprous iodide and ethylmagnesium bromide in THF at -78° C. gives 2-chloro-4-ethyl-5-nitropyrimidine (2). Displacement of the 2-chloro group in 2, is accomplished by treatment with 2-ethyl-4-methylimidazole or imidazole in acetonitrile at room temperature. Reduction of the nitro moiety in 3 to produce 4 is accomplished as illustrated. Reduction of 2,6-dichloro-4-ethyl-5-nitropyrimidine (5) is accomplished as illustrated to produce the compound 4 where R is hydrogen. ##STR6##

Sources & evidence

ORD record
ord-dd9e510580ce4256b39545cf61b077a4
Source dataset
uspto-grants-1994_06
Patent number
US05318975

Reaction notes

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