Aluminium lithium hydride → HCID 57209067, compound

HRID 9908Notes

Reaction equation

HRID 9908 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]2[N:23]=[C:22]([N:24]3[CH2:28][CH2:27][CH2:26][C@H:25]3[C:29](=O)[NH2:30])[N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][N:19]3[CH2:32][CH3:33])[CH:11]=[CH:12][CH:13]=1>C1COCC1>[NH2:30][CH2:29][C@@H:25]1[CH2:26][CH2:27][CH2:28][N:24]1[C:22]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:32][CH3:33])=[C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=2)[N:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 695863026-(3-chloro-phenyl-amino)-9-ethyl-[(S)-2-carbamoyl-pyrrolidin-1-yl]-9H-purine

Product 1

HCID 57209067HCID 57209067, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 230 mg (6.07 mmol) of LiAlH4 in 5 ml of abs. THF is added dropwise to a suspension of 600 mg (1.6 mmol) of 6-(3-chloro-phenyl-amino)-9-ethyl-[(S)-2-carbamoyl-pyrrolidin-1-yl]-9H-purine (cf. Example 64) in 15 ml of abs. THF, and the mixture is stirred at 80° C. for 24 h. Thereafter, 10 ml of ice/water are cautiously added dropwise and the reaction mixture is poured onto 50 ml of ice/water. The mixture is extracted three times with ethyl acetate (100 ml each time). The combined organic extracts are washed with aqueous sodium bicarbonate solution, water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated under reduced pressure. The resulting crude product (oil) is purified by means of column chromatography (silica gel), digestion in diethyl ether/hexane and RP-MPLC (medium pressure chromatography, Lichroprep® RP-18 (irregular silica gel support material, Merck, Darmstadt, Germany)). 2-[(S)-2-Aminomethyl-pyrrolidin-1-yl]-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine is obtained as an oil; FAB-MS: (M+H)+=372, HPLC: tret (grad20/2)=11.25 minutes; [α]D20=−56.1° [DMSO, c=0.51].

Workup

  1. extractionThe mixture is extracted three times with ethyl acetate (100 ml each time)
  2. washThe combined organic extracts are washed with aqueous sodium bicarbonate solution, water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe resulting crude product (oil) is purified by means of column chromatography (silica gel), digestion in diethyl ether/hexane

Sources & evidence

ORD record
ord-badd9b1876bd40f3979aa10f70c6a780
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Reaction notes

Loading…