1-Propanol → (S)-2-Benzyl-7-phenyl-5-propoxy-2,7-dihydro-3H-imidazo[1,2-c]pyrazolo[4,3-e]pyrimidine

HRID 973769Notes

Reaction equation

HRID 973769 reaction equation
[Na].[C:2]1([N:8]2[C:16]3[N:15]=[C:14](Cl)[N:13]4[CH2:18][C@H:19]([CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:20]=[C:12]4[C:11]=3[CH:10]=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[Cl-].[CH2:30]([OH:33])[CH2:31][CH3:32]>>[C:2]1([N:8]2[C:16]3[N:15]=[C:14]([O:33][CH2:30][CH2:31][CH3:32])[N:13]4[CH2:18][C@H:19]([CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:20]=[C:12]4[C:11]=3[CH:10]=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 10311-PropanolHCID 5234Sodium ChlorideHCID 5360545SodiumHCID 15667137(S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-5-chloro-3H-imidazo[1,2-c]pyrazolo-[4,3-e]pyrimidine

Product 1

HCID 15667141(S)-2-Benzyl-7-phenyl-5-propoxy-2,7-dihydro-3H-imidazo[1,2-c]pyrazolo[4,3-e]pyrimidineYield 75%

Procedure

Then, 20 mg sodium was reacted in 3 ml n-propanol. The solution was cooled with an ice bath and 209 mg of the above product (S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-5-chloro-3H-imidazo[1,2-c]pyrazolo[4,3-e]pyrimidine was added with stirring. After 1 hour the reaction was poured into 100 ml saturated NaCl solution and extracted with 200 ml CHCl3. The organic layer was dried over MgSO4, filtered and concentrated to yield an oil which was purified by radial chromatography (5-10% MeOH/ CHCl3, 2 mm plate) to yield 168 mg of (S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-5-propoxy-3H-imidazo[1,2-c]pyrazolo[4,3-e]pyrimidine (75%).

Workup

  1. temperatureThe solution was cooled with an ice bath
  2. extractionextracted with 200 ml CHCl3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield an oil which
  7. customwas purified by radial chromatography (5-10% MeOH/ CHCl3, 2 mm plate)

Sources & evidence

ORD record
ord-0e3cd134b63d4810b48a88827a5b534c
Source dataset
uspto-grants-1991_11
Patent number
US05064947

Reaction notes

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