N-(4-cyano-phenyl)-2-{4-[6-oxo-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-6,7-dihydro-1H-purin-8-yl]-phenoxy}-acetamide → N-(4-cyano-phenyl)-2-[4-(6-oxo-1-propyl-6,7-dihydro-1H-purin-8-yl)-phenoxy]-acetamide

HRID 925543Notes

Reaction equation

HRID 925543 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:40])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:27](COCC[Si](C)(C)C)[C:26]4[C:25](=[O:36])[N:24]([CH2:37][CH2:38][CH3:39])[CH:23]=[N:22][C:21]=4[N:20]=3)=[CH:15][CH:14]=2)=[CH:5][CH:4]=1)#[N:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:40])[CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[NH:27][C:26]4[C:25](=[O:36])[N:24]([CH2:37][CH2:38][CH3:39])[CH:23]=[N:22][C:21]=4[N:20]=3)=[CH:17][CH:18]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 67134763N-(4-cyano-phenyl)-2-{4-[6-oxo-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-6,7-dihydro-1H-purin-8-yl]-phenoxy}-acetamide

Product 1

HCID 67134905N-(4-cyano-phenyl)-2-[4-(6-oxo-1-propyl-6,7-dihydro-1H-purin-8-yl)-phenoxy]-acetamideYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The above compound N-(4-Cyano-phenyl)-2-{4-[6-oxo-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-6,7-dihydro-1H-purin-8-yl]-phenoxy}-acetamide (0.110 g, 0.20 mmol) was taken in DCM (6 ml) and TFA (3 ml), stirred for 4 hrs. at 27° C. The solvent was evaporated and the residue was washed with saturated NaHCO3 followed by water and n-pentane to obtain N-(4-cyano-phenyl)-2-[4-(6-oxo-1-propyl-6,7-dihydro-1H-purin-8-yl)-phenoxy]-acetamide (0.049 g, 58%).

Workup

  1. customat 27° C
  2. customThe solvent was evaporated
  3. washthe residue was washed with saturated NaHCO3

Sources & evidence

ORD record
ord-9ab12cf24cc54079bbeb3f4e03eaf7f2
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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