Hydrochloric Acid → 9-Benzyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 2111310Notes

Reaction equation

HRID 2111310 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][N:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]([Cl:17])[N:9]=1)C.Cl>C(O)C>[CH2:18]([N:7]1[CH2:6][CH2:5][C:4](=[O:3])[NH:14][C:13]2[CH:12]=[N:11][C:10]([Cl:17])=[N:9][C:8]1=2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 581541303-[Benzyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-propanoic acid ethyl ester

Product 1

HCID 581541759-Benzyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneYield 18.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.1 g (0.003 mole) of 3-[benzyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-propanoic acid ethyl ester (IV-22) in 20 mL of ethanol was added 1.7 g (0.0075 mole) of stannous chloride dehydrate and 0.5 mL of hydrochloric acid. The mixture was heated at 60 degrees for 2 hrs. The solvent was evaporated under reduced pressure. The residue was taken up in 50 mL of water and extracted three times with 50 mL of ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-methanol (100:0-95:5) gave 0.16 g of 9-benzyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-22) as a white solid.

Workup

  1. temperatureThe mixture was heated at 60 degrees for 2 hrs
  2. customThe solvent was evaporated under reduced pressure
  3. extractionextracted three times with 50 mL of ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography
  8. washeluting with dichloromethane-methanol (100:0-95:5)

Sources & evidence

ORD record
ord-27855efd5a2d4075a7f4a1ed46050597
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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