Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Urea | HCID 1176 | — |
| Reactant | Pyrimidine | HCID 9260 | — |
| Reactant | 4-Iodoaniline | HCID 10893 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 6-Methyl-2,4-pyrimidinediamine | HCID 229743 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 54327178 | HCID 54327178 | — |
Reaction Steps
A solution of 2,4-diamino-6-methyl pyrimidine (1.0 gm) in water (60 ml) was cooled to 0° C in ice-salt bath and stirred mechanically. p-Iodo aniline (1.84 gm) was dissolved in ethanol (30 ml) and to this solution 3 N HCl (30 ml) was added. The solution was then cooled to -5° C. A solution of sodium nitrite (0.567 gm) in water (5 ml) was also cooled to 0° C. The sodium nitrite solution was then added to the p-iodo aniline solution. After shaking thoroughly, excess sodium nitrite was decomposed with a pinch of urea. The diazotized p-iodo aniline was then added to the pyrimidine solution. After stirring for ten minutes, the pH of the combined solution was adjusted to 7.0 with 30 percent sodium hydroxide. A precipitate appeared. After stirring two hours more, the product was filtered, dried in vacuum desiccator, and crystallized from ethanol. M.P. 243°-44° C. Yield: 2.5 gm (90 percent).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04083841 |
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| Source dataset | uspto-grants-1978_04 |
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| ORD ID | ord-82d5eefb318140829abf34ca1aeb4ded |
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| Source note | uspto-grants-1978_04 |
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