HCID 69558414, compound → HCID 69558443, compound

HRID 1934449Notes

Reaction equation

HRID 1934449 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]([Cl:26])[CH:21]=3)[C:8]=2[N:9]=[C:10](SC)[N:11]=1>C(OCC)(=O)C.CO.C(Cl)Cl.[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]([Cl:26])[CH:21]=3)[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

6

Reactant 1

HCID 69558414HCID 69558414, compound

Product 1

HCID 69558443HCID 69558443, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 186 mg (0.458 mmol) of [[2-(methylthio)-6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 4 mL of ethyl acetate and 1 mL of methanol was heated to reflux and treated with 1.05 g of Raney Ni in portions over 3 hours. The reaction was diluted with 2 mL of methylene chloride and the solids were removed by filtration through a filter aid. The reaction mixture was dried with sodium sulfate and concentrated to provide 140 mg (85%) of [[6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a solid. nmr (500 MHz, CDCl3) δ1.29 (t, J=7.4 Hz, 3H), 2.62 (q, J=7.4 Hz, 2H), 3.80 (s, 3H), 5.09 (s, 2H), 5.42 (s, 2H), 6.41 (s, 1H), 6.88 (d, J=6.9 Hz, 1H),. 7.04 (s, 1H), 7.21 (m, 2H), 8.38 (s, 1H)

Workup

  1. temperatureto reflux
  2. customthe solids were removed by filtration through a filter aid
  3. dry with materialThe reaction mixture was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e15237fc8d9d45b889d1ad4c8c9d3269
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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