Methanol → HCID 70269420, compound

HRID 2285520Notes

Reaction equation

HRID 2285520 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[N:9](C(=O)C)[CH2:10][CH2:11][N:12]=2)=[C:6](Cl)[N:5]([NH2:17])[CH:4]([CH3:18])[N:3]=1.[CH3:19][OH:20]>>[Cl:1][C:2]1[C:7]([C:8]2[NH:9][CH2:10][CH2:11][N:12]=2)=[C:6]([O:20][CH3:19])[N:5]([NH2:17])[CH:4]([CH3:18])[N:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 67367667HCID 67367667, compound

Product 1

HCID 70269420HCID 70269420, compoundYield 80%

Procedure

10.0 g 4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine are boiled in 400 ml methanol for 48 hours under reflux. The solution is concentrated, and the residue mixed with warm tetrahydrofuran. The crystals are recrystallized from isopropanol/ether. 6.4 g (80%) of 4-chloro-6-methoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine is obtained as the hydrochloride, melting point 189° C. Melting point of the base 217°-219° C. (decomposition). 1H-NMR spectrum is DMSO-d6, delta values in ppm: 2.53 (s, CH3), 3.65 (s, N-CH2 --CH2 -N), 3.98 (s, OCH3), 8.66 (twice NH, deuterizable).

Workup

  1. temperatureunder reflux
  2. concentrationThe solution is concentrated
  3. additionthe residue mixed with warm tetrahydrofuran
  4. customThe crystals are recrystallized from isopropanol/ether

Sources & evidence

ORD record
ord-8fb15e18b3024e79ac101f1c32f890ce
Source dataset
uspto-grants-1982_04
Patent number
US04323570

Reaction notes

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