Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Carbonic acid-guanidine (1:1) | HCID 286947 | — |
| Reactant | HCID 54460384 | HCID 54460384 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Sodium Methoxide | HCID 10942334 | — |
| Product | Ormetoprim | HCID 23418 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07858632B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-924dedfba4874874b5eaf5279be6303c |
|---|
| Source note | uspto-grants-2010_12 |
|---|
