Propanal → HCID 67598026, compound

HRID 1738803Notes

Reaction equation

HRID 1738803 reaction equation
C(N[CH2:4][C:5]#[C:6][C:7]([OH:28])([CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[N:17][C:16]=2[N:15]([CH3:26])[C:13]1=[O:14])C.[CH:29](=O)[CH2:30][CH3:31].C([BH3-])#[N:34].[Na+].[CH2:37](O)[CH3:38]>>[CH2:37]([CH2:4][C:5]#[C:6][C:7]([OH:28])([CH3:27])[CH2:8][CH2:9][CH2:10][CH:11]([NH:34][CH2:29][CH2:30][CH3:31])[N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[N:17][C:16]=2[N:15]([CH3:26])[C:13]1=[O:14])[CH3:38]

Participants

5

Reactant 4

HCID 527Propanal2×HCID 702EthanolHCID 5003444Sodium cyanoborohydride3×HCID 21839339HCID 21839339, compound

Product 1

HCID 67598026HCID 67598026, compound

Conditions

Temperature
-78 °C

Procedure

650 mg (1.67 mmol) of 1-(8-ethylamino-5-hydroxy-5-methyl-6-octynyl)-3-methyl-7-propylxanthine from Example 23 were dissolved in 30 ml of ethanol. After cooling to -78° C., 602 μl (8.34 mmol) of propionaldehyde were added and, after warming to 0° C., 105 mg (1.67 mmol) of sodium cyanoborohydride were added. In order to complete the reaction, a spatula tip of sodium cyanoborohydride was added after 2 hours, and a further 602 μl (8.34 mmol) of propionaldehyde and 105 mg (1.67 mmol) of sodium cyanoborohydride were added after 3 hours. After the reaction was complete, the reaction mixture was concentrated in a rotary evaporator under reduced pressure, sodium bicarbonate solution was added to the residue, the aqueous phase was extracted with dichloromethane, the combined extracts were dried with magnesium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure in a rotary evaporator. The crude product was purified by flash chromatography with the mobile phase mixture dichloromethane/methane/saturated ammonia solution=19/1/0.02.

Workup

  1. temperatureafter warming to 0° C.
  2. customthe reaction
  3. concentrationthe reaction mixture was concentrated in a rotary evaporator under reduced pressure, sodium bicarbonate solution
  4. additionwas added to the residue
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. dry with materialthe combined extracts were dried with magnesium sulfate
  7. filtrationthe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure in a rotary evaporator
  9. customThe crude product was purified by flash chromatography with the mobile phase mixture dichloromethane/methane/saturated ammonia solution=19/1/0.02

Sources & evidence

ORD record
ord-bbd660db9a2f4c81ada55bb8ba4f806f
Source dataset
uspto-grants-1999_10
Patent number
US05965555

Reaction notes

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