HCID 87617944, compound → HCID 87618405, compound

HRID 2111344Notes

Reaction equation

HRID 2111344 reaction equation
C[O:2][C:3](=O)[CH:4]([CH3:24])[CH2:5][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][N:10]=[C:9]([Cl:16])[N:8]=1>C(O)(=O)C.[Fe]>[CH2:17]([N:6]1[CH2:5][CH:4]([CH3:24])[C:3](=[O:2])[NH:13][C:12]2[CH:11]=[N:10][C:9]([Cl:16])=[N:8][C:7]1=2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 87617944HCID 87617944, compound

Product 1

HCID 87618405HCID 87618405, compoundYield 28.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2.55 g (0.007 mole) of (rac)-3-[benzyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-2-methyl-propanoic acid methyl ester in 50 mL of acetic acid, was added 2.550 g (0.0457 g-atom) of iron powder. The mixture was heated at 80 degrees for 2 hours, then filtered through Celite while still hot. The filtercake was washed with 200 mL of ethyl acetate, and the combined filtrate washed successively with 200 mL of water, 200 mL of 7.4 M ammonium hydroxide, 200 mL of water and 200 mL of brine. The aqueous layers were extracted with 200 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 recrystallized from dichloromethane—hexanes to give 0.61 g of (rac)-9-benzyl-2-chloro-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-42) as off-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 200 mL of ethyl acetate
  4. washthe combined filtrate washed successively with 200 mL of water, 200 mL of 7.4 M ammonium hydroxide, 200 mL of water and 200 mL of brine
  5. extractionThe aqueous layers were extracted with 200 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 recrystallized from dichloromethane—hexanes

Sources & evidence

ORD record
ord-543fb27a35c2491f9137babca7027c6f
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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