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

HRID 1285189Notes

Reaction equation

HRID 1285189 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4bda55f5a40347509669f712b959d515
Source dataset
uspto-grants-1986_01
Patent number
US04565864

Reaction notes

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