HCID 57593504, compound → HCID 10435801, compound

HRID 1785320Notes

Reaction equation

HRID 1785320 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:14]([C:32]([O:34]C(C)C)=O)=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>O1CCCC1>[C:26]1([CH2:25][O:24][C:22](=[O:23])[NH:21][CH2:20][CH2:19][CH2:18][NH:17][C:15]2[C:14]([CH2:32][OH:34])=[CH:13][N:12]=[C:11]([NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([NH:1][C:22]([NH:21][CH2:20][CH3:19])=[O:23])[CH:5]=3)[N:16]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 1

HCID 57593504HCID 57593504, compound

Product 1

HCID 10435801HCID 10435801, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-Methylethyl 2-[(3-nitrophenyl)amino]-4-[[3-[[(phenylmethoxy)carbonyl]amino]propyl]amino]pyrimidine-5-carboxylate (1.7 g) in tetrahydrofuran (100 ml) LiAlH4 (410 mg) was added in portions at 0° C. After 6 h at 0° C. the reaction was quenched by addition of saturated ammonium chloride solution. Ethyl acetate was added and the mixture filtered. After evaporation of the filtrate the residue was partitioned between water and dichloromethane. The organic layer was washed with brine, dried (Na2SO4), filtered and evaporated. Chromatography of the residue on silica gel (dichloromethane/methanol)) yielded the title compound (650 mg).

Workup

  1. customAfter 6 h at 0° C. the reaction was quenched by addition of saturated ammonium chloride solution
  2. additionEthyl acetate was added
  3. filtrationthe mixture filtered
  4. customAfter evaporation of the filtrate the residue
  5. customwas partitioned between water and dichloromethane
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-bb73efa892f046989ff7f735192fbd01
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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