Guanidine → 5-[(4-Chloro-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine

HRID 2398063Notes

Reaction equation

HRID 2398063 reaction equation
CO[CH:3](OC)[CH:4]([C:17]#[N:18])[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([Cl:14])=[C:8]([O:15][CH3:16])[CH:7]=1.[NH2:21][C:22]([NH2:24])=[NH:23]>>[NH2:23][C:22]1[N:24]=[C:17]([NH2:18])[C:4]([CH2:5][C:6]2[CH:7]=[C:8]([O:15][CH3:16])[C:9]([Cl:14])=[C:10]([O:12][CH3:13])[CH:11]=2)=[CH:3][N:21]=1

Participants

3

Reactant 2

HCID 3520GuanidineHCID 203664024-Chloro-α-(dimethoxymethyl)-3,5-dimethoxybenzenepropanenitrile

Product 1

HCID 123984585-[(4-Chloro-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine

Procedure

21 G. of 4-chloro-3,5-dimethoxy-α -cyano-hydrocinnamaldehyde dimethyl acetal were heated to reflux for 1.5 hours with 140 ml. of a 1N methanolic guanidine solution. The solvent was then removed by distillation on an oil bath at 160° C. and the residue heated for 15-20 minutes at this temperature until completely solidified to a crystalline mass. The mass was slurried with 80-100 ml. of water and removed by filtration under suction, whereby there was obtained 2,4-diamino-5-(4-chloro-3,5-dimethoxybenzyl)-pyrimidine of melting point 218° C.

Workup

  1. temperatureto reflux for 1.5 hours with 140 ml
  2. customThe solvent was then removed by distillation on an oil bath at 160° C.
  3. temperaturethe residue heated for 15-20 minutes at this temperature
  4. customof water and removed by filtration under suction

Sources & evidence

ORD record
ord-23f39f4967c144ad98554d16852f6c97
Source dataset
uspto-grants-1977_05
Patent number
US04024145

Reaction notes

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