Water → HCID 178483682, compound

HRID 2052992Notes

Reaction equation

HRID 2052992 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]([C@H:5]1[CH2:8][C@@H:7]([N:9]2[C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH2:18])[C:12]=3[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:20]=3)=[CH:10]2)[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:26]([O:25][C:21]1[CH:20]=[C:19]([C:11]2[C:12]3[C:17]([NH2:18])=[N:16][CH:15]=[N:14][C:13]=3[N:9]([C@H:7]3[CH2:8][C@@H:5]([CH2:3][N:2]([CH3:33])[CH3:1])[CH2:6]3)[CH:10]=2)[CH:24]=[CH:23][CH:22]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178484582HCID 178484582, compound

Product 1

HCID 178483682HCID 178483682, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 42 mg (0.095 mmol) of cis-3-[4-amino-5-(3-benzyloxy-phenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid dimethylamide in 2 ml of anhydrous THF is added dropwise at 0° C. to a 10 mg of lithium aluminium hydride suspended in 2 ml of anhydrous THF. The reaction mixture is slowly warmed to RT overnight. For working-up, the reaction mixture is cooled to 0° C. and then water and a 15% NaOH solution are added in succession thereto. The solution is partitioned between water and ethyl acetate. Drying the organic layer over magnesium sulfate, concentrating in vacuo and purifying by medium-pressure liquid chromatography yield cis-5-(3-benzyloxy-phenyl)-7-(3-dimethylaminomethyl-cyclobutyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine. Analytical HPLC: tR=5.98 min (Grad 2); ES-MS: m/eo=428.1.

Workup

  1. temperaturethe reaction mixture is cooled to 0° C.
  2. customThe solution is partitioned between water and ethyl acetate
  3. dry with materialDrying the organic layer over magnesium sulfate
  4. concentrationconcentrating in vacuo
  5. custompurifying by medium-pressure liquid chromatography

Sources & evidence

ORD record
ord-ac5531d2b6d74b2495e67d393f6aa1e4
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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