Ammonia → HCID 90816626, compound

HRID 1785322Notes

Reaction equation

HRID 1785322 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:40])[NH:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]2[C:20]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:19][N:18]=[C:17]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-])=O)[CH:32]=3)[N:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N.O>C(O)C>[C:1]1([CH2:7][O:8][C:9](=[O:40])[NH:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]2[C:20]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:19][N:18]=[C:17]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=3)[N:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 131727365HCID 131727365, compound

Product 1

HCID 90816626HCID 90816626, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenylmethyl[3-[[5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-[(3-nitrophenyl)amino]pyrimidin-4-yl]amino]propyl]carbamate (244 mg), dissolved in ethanol (30 ml), was slowly added to a mixture of FeSO4 heptahydrate (1.25 g), concentrated ammonia solution (25%; 1.25 ml) and water (5 ml). After refluxing for 3 h the mixture was filtered and the filter cake washed with ethyl acetate. The filtrate was washed with water and brine, dried (Na2SO4), filtered and evaporated to yield the crude title compound (230 mg), which was used in the next step without further purification.

Workup

  1. temperatureAfter refluxing for 3 h the mixture
  2. filtrationwas filtered
  3. washthe filter cake washed with ethyl acetate
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-09cb6bfd4238434398cf6768dc9852a4
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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