Ethyl Acetate → HCID 178503797, compound

HRID 892116Notes

Reaction equation

HRID 892116 reaction equation
[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2Cl)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][S:27][CH:28](C)CO.[H-].[Na+].C([O:37][CH2:38][CH3:39])(=O)C>O1CCCC1>[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2[O:37][CH2:38][CH2:39][CH2:26][S:27][CH3:28])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 130395652-(Methylsulfanyl)propan-1-olHCID 178478320(8R)-8-benzyl-5-chloro-2-cyclopentyl-7,8-dihydro-1H-imidazo[2,1-f]purine2×

Product 1

HCID 178503797HCID 178503797, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 67a (240 mg, 0.585 mmol) obtained in Example 67 in tetrahydrofuran (2 mL) were added 2-methylthiopropanol (1 mL) and sodium hydride (containing 34% mineral oil, 88 mg, 2.34 mmol), then Compound 67a (240 mg, 0.585 mmol) was further added to the mixture, and stirring was continued at 100° C. for 4 hours. To the reaction mixture was added ethyl acetate, and the mixture was washed twice with water and dried over magnesium sulfate. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (chloroform:methanol=99:1) to obtain the title compound (100 mg, 40%) as an ocher foamy solid.

Workup

  1. washthe mixture was washed twice with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-00725e3dbf5c496998a45d884879d53d
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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