Water → 4,6-Diamino-1,2-dihydro-1-hydroxy-2,2-dimethyl-1,3,5-triazine hydrochloride

HRID 1463283Notes

Reaction equation

HRID 1463283 reaction equation
[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[N:6]([O:10]CC2C=CC=CC=2)[C:5]([CH3:19])([CH3:18])[N:4]=1.O>C(O)C.[Pd]>[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[N:6]([OH:10])[C:5]([CH3:19])([CH3:18])[N:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 190899234,6-Diamino-1,2-dihydro-1-phenylmethoxy-2,2-dimethyl-1,3,5-triazine hydrochloride

Product 1

HCID 190899214,6-Diamino-1,2-dihydro-1-hydroxy-2,2-dimethyl-1,3,5-triazine hydrochlorideYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.0 grams (0.035 mole) of 4,6-diamino-1,2-dihydro-1-phenylmethoxy-2,2-dimethyl-1,3,5-triazine hydrochloride and 20 ml of water in 30 ml of ethanol was hydrogenated in the presence of 1.0 gram of 5% palladium on charcoal using a Parr hydrogenator. Upon completion of the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to a residual solid. The solid was recrystallized from ethanol, yielding 4.7 grams of 4,6-diamino-1,2-dihydro-1-hydroxy-2,2-dimethyl-1,3,5-triazine hydrochloride, m.p. 241° C. (dec.). The NMR spectrum was consistent with the proposed structure. The reaction was repeated several times to provide sufficient material for the next step.

Workup

  1. filtrationUpon completion of the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure to a residual solid
  3. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-a5ee9bb63dd64abab7564936dffd4f93
Source dataset
uspto-grants-1994_04
Patent number
US05300503

Reaction notes

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