HCID 69558084, compound → HCID 69557385, compound

HRID 1934435Notes

Reaction equation

HRID 1934435 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[C:7]2[CH:16]=[C:15]([CH2:17][CH3:18])[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)[C:8]=2[N:9]=[C:10](SC)[N:11]=1>C(O)C.[Ni]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[C:7]2[CH:16]=[C:15]([CH2:17][CH3:18])[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 1

HCID 69558084HCID 69558084, compound

Product 1

HCID 69557385HCID 69557385, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 211 mg (0.541 mmol) of [[2-(methylthio)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 20 mL of ethanol was treated with 1.27 g of Raney Ni and heated to reflux. After 24 hours, the solids were removed by filtration through a filter aid and the reaction concentrated to provide 140 mg (75%) of [[6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a solid. nmr (300 MHz, CDCl3) δ1.20 (t, 3H), 2.62 (q, 2H), 3.79 (s, 3H), 5.09 (s, 2H), 5.45 (s, 2H), 6.42 (s, 1H), 6.72 (d, 1H), 6.82 (d, 1H), 6.93 (dt, 1H), 7.26 (dt, 1H), 8.37 (s, 1H)

Workup

  1. temperatureheated to reflux
  2. customthe solids were removed by filtration through a filter aid
  3. concentrationthe reaction concentrated

Sources & evidence

ORD record
ord-eb2b18a275b7410885c8aa7277b51d3c
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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