Chloroacetaldehyde → 7-Chloro-5-methoxyimidazo[1,2-c]pyrimidine

HRID 2164229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2164229
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.Cl[CH2:12][CH:13]=O.C(=O)(O)[O-].[Na+].C>O.C1C=CC=CC=1>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]2[CH:12]=[CH:13][N:1]=[C:2]2[CH:7]=1

Komponenten

7

Edukt 4

HCID 33ChloroacetaldehydeHCID 297MethaneHCID 516892Sodium BicarbonateHCID 5942484-Amino-6-chloro-2-methoxypyrimidine

Produkt 1

HCID 133942007-Chloro-5-methoxyimidazo[1,2-c]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1.7 g (0.011 mole) of 4-amino-6-chloro-2-methoxypyrimidine and 3.0 g (0.015 mole) of 50% aqueous chloroacetaldehyde in 20 ml of water was heated at 80° C. for one hour, and was then cooled in an ice bath with concomitant neutralization with sodium bicarbonate. The mixture was extracted with three 50 ml portions of chloroform which were then dried over magnesium sulfate and evaporated. The residue obtained was dissolved in boiling benzene, treated with decolorizing charcoal, and filtered. The residue which was obtained by evaporation of the filtrate was triturated with diethyl ether to provide a yellow solid. The solid was purified on a preparative scale high pressure liquid chromatograph, using a mixture of 75% ethyl acetate/25% hexanes as the eluent. Recrystallization from cyclohexane gave white solid 7-chloro-5-methoxyimidazo[1,2-c]pyrimidine, m.p. 115°-118° C. Analysis: Calculated for C7H6H3OCl: %C,45.8; %H, 3.3; %N, 22.9; Found: %C,45.4; %H,3.1; %N,23.4.

Aufarbeitung

  1. extractionThe mixture was extracted with three 50 ml portions of chloroform which
  2. dry with materialwere then dried over magnesium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. dissolutionwas dissolved
  6. filtrationfiltered
  7. customThe residue which was obtained by evaporation of the filtrate
  8. customwas triturated with diethyl ether
  9. customto provide a yellow solid
  10. customThe solid was purified on a preparative scale high pressure liquid chromatograph
  11. additiona mixture of 75% ethyl acetate/25% hexanes as the eluent
  12. customRecrystallization from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-bc5e67be57cc470dad7b00e1442f1c39
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04503050

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