HCID 87619359, compound → HCID 87619004, compound

HRID 2111322Notes

Reaction equation

HRID 2111322 reaction equation
C([O:3][C:4](=O)[CH:5]([CH3:23])[CH2:6][N:7]([C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][N:16]=[C:15]([Cl:22])[N:14]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])C>C(O)(=O)C.[Fe]>[Cl:22][C:15]1[N:16]=[CH:17][C:18]2[NH:19][C:4](=[O:3])[CH:5]([CH3:23])[CH2:6][N:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:13]=2[N:14]=1

Participants

4

Reactant 1

HCID 87619359HCID 87619359, compound

Product 1

HCID 87619004HCID 87619004, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1.06 g (0.0031 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(3-methyl-butyl)-amino]-2-methyl-propionic acid ethyl ester (IV-27) in 20 mL of acetic acid, was added 1.0 g (0.0179 g-atom) of iron powder. The mixture was heated at 80 degrees for 2 hours and then filtered through Celite while still hot. The filtercake was washed with 100 mL of ethyl acetate (100 mL), and the combined filtrate washed successively with 100 mL of water 100 mL of 7.4 M ammonium hydroxide, 100 mL of water and 100 mL of brine. The aqueous layers were extracted with 100 mL of ethyl acetate, and the combined ethyl acetate layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate—dichloromethane (1:1) to give 0.61 g of (rac)-2-chloro-7-methyl-9-(3-methyl-butyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-27) as white crystalline solid.

Workup

  1. temperatureThe mixture was heated at 80 degrees for 2 hours
  2. filtrationfiltered through Celite while still hot
  3. washThe filtercake was washed with 100 mL of ethyl acetate (100 mL)
  4. washthe combined filtrate washed successively with 100 mL of water 100 mL of 7.4 M ammonium hydroxide, 100 mL of water and 100 mL of brine
  5. extractionThe aqueous layers were extracted with 100 mL of ethyl acetate
  6. dry with materialthe combined ethyl acetate layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with ethyl acetate—dichloromethane (1:1)

Sources & evidence

ORD record
ord-db691b7e02ff46d0a4a69b788066746a
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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