Tetramethyltin → HCID 178501317, compound

HRID 2053015Notes

Reaction equation

HRID 2053015 reaction equation
[CH3:1][O:2][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)=[C:10]2Br)[CH2:6]1)=[O:4].[CH3:34][Sn](C)(C)C>CN(C)C=O>[CH3:1][O:2][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)=[C:10]2[CH3:34])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 11661TetramethyltinHCID 178501313HCID 178501313, compound

Product 1

HCID 178501317HCID 178501317, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a sealed tube, 4.68 g (9.02 mmol) trans-3-[4-amino-5-(3-benzyloxy-phenyl)-6-bromo-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid methylester of Example 103, 2.08 g (1.8 mmol) tetrakistriphenylphosphin palladium and 5.3 ml (38.05 mmol) tin tetramethyl (Fluka, Buchs, Switzerland) are heated under Argon in 20 ml dry N,N-dimethylformamide for 30 h at 100-105° C. bath temperature. The reaction mixture is filtered on hyflo (Hyflo Super Cel®; Fluka, Buchs, Switzerland), and the residue washed thouroughly with N,N-dimethylformamide. The dark filtrate is evaporated at 60° C. to dryness, the residual mass dissolved in hot ethyl acetate and chromatographed on silicagel (hexane-ethyl acetate 25:75). The title compound is obtained as yellow crystals. Analytical HPLC: tR=3.54 min (shorty); ES-MS: m/eo=443; NMR (DMSO-d6): 8.08/s (1H), 7.25-7.5/several m's (6H), 6.99/“d” (1H); 6.90/s (1H); 6.85/“d” (1H); 5.09/s (2H); 5.06/m (1H); 3.64/s (3H); 3.2-3.5/2×m (3H); 2.59/m (2H); 2.18/s (3H).

Workup

  1. filtrationThe reaction mixture is filtered on hyflo (Hyflo Super Cel®; Fluka, Buchs, Switzerland)
  2. washthe residue washed thouroughly with N,N-dimethylformamide
  3. customThe dark filtrate is evaporated at 60° C. to dryness
  4. dissolutionthe residual mass dissolved in hot ethyl acetate
  5. customchromatographed on silicagel (hexane-ethyl acetate 25:75)

Sources & evidence

ORD record
ord-674fcdbcb646431cbb6f85ea3db48dff
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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