Imidazole → HCID 131727365, compound

HRID 1785321Notes

Reaction equation

HRID 1785321 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([NH:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[N:7][CH:8]=1.Cl[Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].N1C=CN=C1>CN(C=O)C>[C:27]1([CH2:26][O:25][C:24](=[O:33])[NH:23][CH2:22][CH2:21][CH2:20][NH:19][C:4]2[C:3]([CH2:2][O:1][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=3)[N:5]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57593850HCID 57593850, compound

Product 1

HCID 131727365HCID 131727365, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A DMF solution (5 ml) of phenylmethyl [3-[[5-(hydroxymethyl)-2-[(3-nitrophenyl)amino]pyrimidin-4-yl]amino]propyl]carbamate (250 mg), chloro(1,1-dimethylethyl)dimethylsilane (190 mg) and 1H-imidazole (170 mg) was stirred at room temperature (48 h). After addition of ice water the mixture was extracted with ethyl acetate. The organic layer was washed with water, brine, dried (Na2SO4), filtered and evaporated. Trituration of the residue with diethyl ether yielded the title compound (300 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3967056d9c0a4471a1236afc9b9afaef
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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