Imidazole → HCID 77737378, compound

HRID 50641Notes

Reaction equation

HRID 50641 reaction equation
[C:1]1([CH:7]2[CH2:9][CH:8]2[NH:10][C:11]2[C:12]3[N:23]=[N:22][N:21]([CH:24]4[CH2:28][CH:27]([OH:29])[CH:26]([OH:30])[CH:25]4[OH:31])[C:13]=3[N:14]=[C:15]([S:17][CH2:18][CH2:19][CH3:20])[N:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si](Cl)(C(C)(C)C)(C)[CH3:33].N1C=CN=C1>CN(C)C=O>[CH3:33][N:10]([CH:8]1[CH2:9][CH:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11]1[C:12]2[N:23]=[N:22][N:21]([CH:24]3[CH2:28][CH:27]([OH:29])[CH:26]([OH:30])[CH:25]3[OH:31])[C:13]=2[N:14]=[C:15]([S:17][CH2:18][CH2:19][CH3:20])[N:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2×HCID 777503684-[7-[(2-Phenylcyclopropyl)amino]-5-(propylthio)-3H-[1,2,3]-triazolo[4,5-d]pyrimidin-3-yl]cyclopentane-1,2,3-triol

Product 1

HCID 77737378HCID 77737378, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of step d) (1.79 g), tert-butyldimethylsilylchloride (1.22 g) and imidazole (1.10 g) in N,N-dimethylformamide (3 ml) was stirred at ambient temperature for 24 hours. Further tert-butyldimethylsilylchloride (1.0 g) was added and the mixture stirred for a further 6 hours. The reaction mixture was concentrated in vacuo and the residue purified by chromatography (SiO2, ethyl acetate: hexane 1:20 as eluant) to afford the sub-title compound (2.43 g).

Workup

  1. stirringthe mixture stirred for a further 6 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue purified by chromatography (SiO2, ethyl acetate: hexane 1:20 as eluant)

Sources & evidence

ORD record
ord-9648724a95124abdad16259680ca18a0
Source dataset
uspto-grants-2004_03
Patent number
US06713483B1

Reaction notes

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