Imidazole → HCID 136368766, compound

HRID 1296417Notes

Reaction equation

HRID 1296417 reaction equation
[OH:1][C@H:2]([CH3:22])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[N:13]3[CH2:17][CH2:18][NH:19][C:12]3=[N:11][C:10]=2[N:9]([CH3:20])[C:8]1=[O:21].N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].O>CN(C)C=O>[CH3:20][N:9]1[C:10]2[N:11]=[C:12]3[NH:19][CH2:18][CH2:17][N:13]3[C:14]=2[C:15](=[O:16])[N:7]([CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]([O:1][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH3:22])[C:8]1=[O:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 135522290HCID 135522290, compound

Product 1

HCID 136368766HCID 136368766, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the stirring solution of (R)-7,8-dihydro-3-(5-hydroxyhexyl)-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (CT-13430) (200 mg, 0.65 mmol) and imidazole (68 mg, 1.0 mmol) in dimethylformamide (1 ml) was added tert-butyldimethylsilyl chloride (127 mg, 1.30 mmol). After stirred at room temperature for 16 hours, the reaction mixture was treated with water and extracted with ethyl acetate (2×15 ml). The combined extracts were washed with water (2×5 ml), with saturated aqueous sodium chloride solution (5 ml), and dried over magnesium sulfate. Concentrating under reduced pressure to provide (R)-7,8-dihydro-1-methyl-3-(5-tert-butyldimethylsilyloxyhexyl)-1H-imidazo[2,1-f]-purine-2,4(3H, 6H)-dione (280 mg, 100% yield) as a white powder.

Workup

  1. extractionextracted with ethyl acetate (2×15 ml)
  2. washThe combined extracts were washed with water (2×5 ml), with saturated aqueous sodium chloride solution (5 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentrating under reduced pressure

Sources & evidence

ORD record
ord-f3242e2eaacd4dbc8d6a1070a6e9d969
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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