Hydrochloric Acid → HCID 13608187, compound

HRID 1905877Notes

Reaction equation

HRID 1905877 reaction equation
[CH3:1][N:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([N+:16]([O-])=O)[CH:9]=2)=[CH:6][C:5](=[N:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[N:4]([CH3:29])[C:3]1=[O:30].Cl>CO.[Pd]>[NH2:16][C:10]1[CH:9]=[C:8]([C:7]2[N:2]([CH3:1])[C:3](=[O:30])[N:4]([CH3:29])[C:5](=[N:19][C:20]3[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])[CH:6]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13608192HCID 13608192, compound

Product 1

HCID 13608187HCID 13608187, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3,4-dihydro-1,3-dimethyl-6-(4-methoxy-3-nitrophenyl)-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (0.94 g) in a mixture of methanol (20 ml) and conc. hydrochloric acid (0.4 ml) was added palladium on activated carbon (10%, 0.20 g). The mixture was stirred under hydrogen atmosphere (1 atm) for 2 hours, and filtered. The filtrate was poured into aqueous sodium bicarbonate, and extracted with chloroform. The organic layer was dried over sodium sulfate, and evaporated. The resulting mass was crystallized from ethanol, to give 3,4-dihydro-6-(3-amino-4-methoxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (0.63 g).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was poured into aqueous sodium bicarbonate
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. customThe resulting mass was crystallized from ethanol

Sources & evidence

ORD record
ord-0ffc5350e4ba4e7786af59575c4a14ba
Source dataset
uspto-grants-1987_03
Patent number
US04649142

Reaction notes

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