Methanol → HCID 69155257, compound

HRID 1296418Notes

Reaction equation

HRID 1296418 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][N:7]3[C:6]=2[C:5](=[O:14])[N:4]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])[C:3]1=[O:29].[C:30](OC(=O)C)(=[O:32])[CH3:31].CO>CN(C)C1C=CN=CC=1.ClCCl>[C:30]([N:11]1[C:8]2=[N:9][C:10]3[N:2]([CH3:1])[C:3](=[O:29])[N:4]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH3:20])[C:5](=[O:14])[C:6]=3[N:7]2[CH2:13][CH2:12]1)(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 136368766HCID 136368766, compound

Product 1

HCID 69155257HCID 69155257, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of (R)-7,8-dihydro-1-methyl-3-(5-tert-butyldimethylsilyloxyhexyl)-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (280 mg, 0.65 mmol) and p-dimethylaminopyridine (160 mg, 1.30 mmol) in dichloromethane (10 ml) was added acetic anhydride (100 mg, 0.98 mmol). After stirring at room temperature for 2 hours, the reaction mixture was treated with methanol. After concentration under reduced pressure, the residue was purified by column chromatography on silica gel eluting with ethyl acetate to provide (R)-8-acetyl-7,8-dihydro-1-methyl-3-(5-tert-butyldimethylsilyloxyhexyl)-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (200 mg, 67% yield) as a white powder.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-b6ec933a15bd4b0b8864780c83d540ed
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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