tert-Butanol → HCID 86591945, compound

HRID 1792007Notes

Reaction equation

HRID 1792007 reaction equation
C(O)(C)(C)C.CC(C)([O-])C.[K+].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[N:33]([CH2:34][C:35]#[CH:36])[C:32]3[C:31](=[O:37])[N:30]([CH3:38])[C:29](=[O:39])[N:28]([CH3:40])[C:27]=3[N:26]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>CS(C)=O.O.C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][N:22]([C:25]2[N:33]([CH:34]=[C:35]=[CH2:36])[C:32]3[C:31](=[O:37])[N:30]([CH3:38])[C:29](=[O:39])[N:28]([CH3:40])[C:27]=3[N:26]=2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 86591946HCID 86591946, compound

Product 1

HCID 86591945HCID 86591945, compoundYield 43.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butanol (0.1 ml) and potassium tert-butoxide (0.015 g) were added to a solution of 4-[1,3-dimethyl-2,6-dioxo-7-(2-propynyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (0.402 g) in dimethyl sulfoxide (5 ml), and the reaction mixture was stirred at room temperature for 16 hours. Saturated aqueous solution of ammonium chloride (5 ml) was added, and the reaction solution was poured into ethyl acetate (50 ml) and water (30 ml). The organic layer was washed with 10% aqueous solution of acetic acid (50 ml), saturated aqueous solution of sodium bicarbonate (50 ml), and saturated aqueous solution of sodium chloride (50 ml) in order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation at reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.176 g of the title compound from a fraction eluted with hexane-ethyl acetate (3:7).

Workup

  1. washThe organic layer was washed with 10% aqueous solution of acetic acid (50 ml), saturated aqueous solution of sodium bicarbonate (50 ml), and saturated aqueous solution of sodium chloride (50 ml) in order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation at reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2576c0151bb84e62969ea4f8de3c958c
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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