Ammonium Hydroxide → 1-Pyrrolo[2,3-d]pyrimidin-7-yl-cyclopropanecarboxylic acid methyl ester

HRID 82273Notes

Reaction equation

HRID 82273 reaction equation
[CH3:1][O:2][C:3]([C:5]1([N:8]2[C:12]3[N:13]=[CH:14][N:15]=[C:16](Cl)[C:11]=3[CH:10]=[CH:9]2)[CH2:7][CH2:6]1)=[O:4].[OH-].[NH4+]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1([N:8]2[C:12]3[N:13]=[CH:14][N:15]=[CH:16][C:11]=3[CH:10]=[CH:9]2)[CH2:6][CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 71743167Methyl 1-(4-chloro-7H-pyrrolo[2,3-D]pyrimidin-7-YL)cyclopropanecarboxylate

Product 1

HCID 708174621-Pyrrolo[2,3-d]pyrimidin-7-yl-cyclopropanecarboxylic acid methyl esterYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclopropanecarboxylic acid methyl ester (Preparation 245, 920 mg, 3.65 mmol) in ethanol (20 mL) was degassed with argon for 15 min. Ammonium hydroxide (4 mL) and 10% palladium on charcoal were added and the reaction mixture was stirred at room temperature under hydrogen (balloon pressure) for 5 hours. The reaction mixture was filtered on a celite bed, washed with ethanol (2×10 mL) and the filtrate was evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of DCM:methanol 100:0 to 98:2) to afford the title compound as a gum in 59% yield, 470 mg.

Workup

  1. filtrationThe reaction mixture was filtered on a celite bed
  2. washwashed with ethanol (2×10 mL)
  3. customthe filtrate was evaporated in vacuo
  4. customThe crude material was purified by column chromatography on silica gel (gradient of DCM:methanol 100:0 to 98:2)

Sources & evidence

ORD record
ord-5f3f55adba554cae8d30f509840b35af
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…