Methanol → Ormetoprim

HRID 2266083Notes

Reaction equation

HRID 2266083 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].CO.[CH3:11][O:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH:21]=[C:22]([CH2:25]OC)[C:23]#[N:24])=[C:15]([CH3:28])[CH:14]=1>C[O-].[Na+].CS(C)=O>[CH3:11][O:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH2:21][C:22]2[C:23]([NH2:24])=[N:7][C:6]([NH2:8])=[N:5][CH:25]=2)=[C:15]([CH3:28])[CH:14]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 286947Carbonic acid-guanidine (1:1)HCID 54460384HCID 54460384, compound

Product 1

HCID 23418Ormetoprim

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
85 °C

Procedure

In step 2, 3-(4,5-dimethoxy-2-methyl-phenyl)-2-methoxymethyl-acrylonitrile and sodium methoxide were dissolved in dry DMSO and stirred for 3.5 hours at 85° C. under nitrogen. Guanidine carbonate was then added to the stirring solution, after which the temperature was raised to 125° C. for three hours, during which methanol removed via a Dean-Stark trap. The solution was cooled to room temperature, diluted with water, and the crude filtrate was recrystallized in DMF to yield 5-(4,5-dimethoxy-2-methyl-benzyl)-pyrimidine-2,4-diamine as a white solid. Mp: 232° C. Mass Spec (M+H): 275.

Workup

  1. customremoved via a Dean-Stark trap
  2. temperatureThe solution was cooled to room temperature
  3. additiondiluted with water
  4. customthe crude filtrate was recrystallized in DMF

Sources & evidence

ORD record
ord-924dedfba4874874b5eaf5279be6303c
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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