Water → HCID 131722562, compound

HRID 1977173Notes

Reaction equation

HRID 1977173 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[N:12][CH:13]=1)[CH3:4].[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17].O>C(O)C>[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[N:12][CH:13]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[N:12][CH:13]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9812914HCID 9812914, compound

Product 1

HCID 131722562HCID 131722562, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a warm solution of (4E)-N-methyl-5-(5-pyrimidinyl)-4-penten-2-amine (258.6 mg, 1.46 mmol) in absolute ethanol (2.3 mL) was added galactaric acid (153.3 mg, 0.73 mmol). Water (0.8 mL) was added, and the solution was heated to near reflux until most of the solids dissolved. The solution was filtered through glass wool to remove a few white, insoluble particles, washing the filter plug with a warm solution of ethanol-water (4:1, v/v) (1.1 mL). The filtrate was diluted with ethanol (6.5 mL), cooled to ambient temperature, and further cooled at 5° C. for 48 h. The white precipitate was filtered, washed with cold ethanol, and vacuum dried at 40° C. for 18 h. The yield was 390.6 mg (94.8%) of a fluffy, white, crystalline powder, mp 164-167° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureto near reflux until most of the solids
  3. dissolutiondissolved
  4. filtrationThe solution was filtered through glass wool
  5. customto remove a few white, insoluble particles
  6. washwashing the filter plug with a warm solution of ethanol-water (4:1
  7. additionThe filtrate was diluted with ethanol (6.5 mL)
  8. temperaturefurther cooled at 5° C. for 48 h
  9. filtrationThe white precipitate was filtered
  10. washwashed with cold ethanol, and vacuum
  11. customdried at 40° C. for 18 h

Sources & evidence

ORD record
ord-8c718ee9a94e4d318e76e0de041c9452
Source dataset
uspto-grants-2001_05
Patent number
US06232316B1

Reaction notes

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