HCID 87619576, compound → HCID 87555658, compound

HRID 2111374Notes

Reaction equation

HRID 2111374 reaction equation
C([O:3][C:4](=O)[CH:5]([CH3:24])[CH2:6][N:7]([C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([Cl:23])[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C>[Pd].C(OCC)(=O)C>[Cl:23][C:16]1[N:17]=[CH:18][C:19]2[NH:20][C:4](=[O:3])[CH:5]([CH3:24])[CH2:6][N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[N:15]=1

Participants

4

Reactant 1

HCID 87619576HCID 87619576, compound

Product 1

HCID 87555658HCID 87555658, compoundYield 3.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.44 g (0.00395 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-phenyl-amino]-2-methyl-propanoic acid ethyl ester (IV-51), 0.35 g of 10% palladium on carbon and 30 mL of ethyl acetate was stirred under an atmosphere of hydrogen for 1 day. The mixture was filtered, and then concentrated under reduced pressure. The residue was dissolved in 10 mL of a 20:80 mixture acetic acid—ethyl acetate and heated to reflux for 18 hours. The mixture was then cooled, concentrated under reduced pressure. The residue was diluted with dichloromethane and washed twice with saturated sodium bicarbonate and then brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hot ethyl acetate and dried to give 0.043 g of (rac)-2-chloro-7-methyl-9-phenyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-51) as white powder.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 10 mL of a 20:80 mixture acetic acid—ethyl acetate
  4. temperatureheated
  5. temperatureto reflux for 18 hours
  6. temperatureThe mixture was then cooled
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was diluted with dichloromethane
  9. washwashed twice with saturated sodium bicarbonate
  10. dry with materialbrine, dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. washThe residue was washed with hot ethyl acetate
  13. customdried

Sources & evidence

ORD record
ord-bd051a9242c646948be60fdc8e087104
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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