Imidazole → HCID 22257998, compound

HRID 567918Notes

Reaction equation

HRID 567918 reaction equation
[CH3:1][Si:2](Cl)([CH3:7])[C:3]([CH3:6])([CH3:5])[CH3:4].N1C=CN=C1.[OH:14][CH:15]([C:26]1[S:41][C:29]2[N:30]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:31](=[O:36])[N:32]([CH3:35])[C:33](=[O:34])[C:28]=2[CH:27]=1)[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH3:1][Si:2]([CH3:7])([C:3]([CH3:6])([CH3:5])[CH3:4])[O:14][CH:15]([C:26]1[S:41][C:29]2[N:30]([CH2:37][CH:38]([CH3:39])[CH3:40])[C:31](=[O:36])[N:32]([CH3:35])[C:33](=[O:34])[C:28]=2[CH:27]=1)[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22257994HCID 22257994, compound

Product 1

HCID 22257998HCID 22257998, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl-(1,1-dimethylethyl)silyl chloride (230 mg) and imidazole (130 mg) were added to a solution of (±)6-(1-hydroxy-1-[1-naphthalenyl]methyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione (500 mg) in dimethylformamide (10 ml). The solution was stirred at ambient temperature for 3 days. The reaction mixture was quenched with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was separated and washed twice with dilute hydrochloric acid and once with brine, dried over magnesium sulfate and concentrated in vacuo. Purification by chromatography on silica gel eluting with isohexane:ethyl acetate (4:1 to 2:1) gave the subtitle product (0.47 g).

Workup

  1. customThe reaction mixture was quenched with dilute hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed twice with dilute hydrochloric acid and once with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel eluting with isohexane:ethyl acetate (4:1 to 2:1)

Sources & evidence

ORD record
ord-ca9547e01e4b43fa8ba50d9b97843804
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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