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Tetrahydrofuran → HCID 44385064, compound

HRID 9906
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Reaction equation

HRID 9906 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[C:12]([C@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[CH2:29][CH3:30])=[C:22]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[N:21]=1)(=O)[NH2:13]>O>[NH2:13][CH2:12][C@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[CH2:29][CH3:30])=[C:22]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[N:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydride2×HCID 695861852-[(R)-(-)-2-carbamoyl-pyrrolidin-1-yl]-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine

Product 1

HCID 44385064HCID 44385064, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 56 mg (1.47 mmol) of LiAlH4 in 2 ml of abs. THF is added to a suspension of 150 mg of 2-[(R)-(−)-2-carbamoyl-pyrrolidin-1-yl]-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine (cf. Example 45) in 10 ml of abs. THF and the mixture is stirred at 80° C. for 22 h. After further addition of 56 mg of LiAlH4, the mixture is allowed to react further for 18 h. 5 ml of WATER are then added dropwise, with ice/water cooling, and the reaction mixture is then poured onto 50 ml of ice/water. The mixture is extracted three times with ethyl acetate. The combined organic extracts are washed twice with water and once with saturated sodium chloride solution and dried over magnesium sulfate. After filtration, the filtrate is concentrated under reduced pressure. The resulting crude product (oil) is purified by means of column chromatography and digestion in diisopropyl ether. 2-[(R)-2-Aminomethyl-pyrrolidin-1-yl]-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine is obtained; m.p. 126–129° C.; FAB-MS: (M+H)+=372, HPLC: tret (grad20/2)=11.09 minutes.

Workup

  1. customto react further for 18 h
  2. extractionThe mixture is extracted three times with ethyl acetate
  3. washThe combined organic extracts are washed twice with water and once with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe resulting crude product (oil) is purified by means of column chromatography and digestion in diisopropyl ether

Sources & evidence

ORD record
ord-5ef4aabf87cb4b2fa299fa5c108e3467
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091346B1

Reaction notes

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