Water → HCID 58315460, compound

HRID 1483141Notes

Reaction equation

HRID 1483141 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:20]([CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].O.[C:30](=O)(O)[O-].[Na+]>C1COCC1.C[Mg]I>[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:20]([CH:21]2[CH2:26][CH2:25][C:24]([OH:27])([CH3:30])[CH2:23][CH2:22]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 67239800N,N-Dimethyl-7-(4-oxocyclohexyl)-2-(2-pyridinylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Product 1

HCID 58315460HCID 58315460, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 178418373HCID 178418373, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-oxo-cyclohexyl)-2-(pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (25 mg, 0.066 mmol) in THF is added 20 drops of MeMgI. After reaction is completed, added 25 mL of water then 30 mL of aqueous sodium bicarbonate. Extraction with dichloromethane (3×50 mL) and concentrated to give a mixture of diastereomers. Preparative HPLC to give 7-(4-hydroxy-4-methyl-cyclohexyl)-2-(pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (2 mg, 4%). MS (ESI) m/z 395.3 (M+H)+

Workup

  1. customAfter reaction
  2. extractionExtraction with dichloromethane (3×50 mL)
  3. concentrationconcentrated
  4. customto give
  5. additiona mixture of diastereomers

Sources & evidence

ORD record
ord-93f4638a9e0d41eb803d9a70b333cb2e
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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