HCID 86623407, compound → HCID 86346256, compound

HRID 2111315Notes

Reaction equation

HRID 2111315 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][N:7]([C:12]1[C:17]([N+:18]([O-])=O)=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=1)[CH:8]1[CH2:11][CH2:10][CH2:9]1)C>C(OCC)(=O)C.Cl.O>[Cl:21][C:14]1[N:15]=[CH:16][C:17]2[NH:18][C:4](=[O:3])[CH2:5][CH2:6][N:7]([CH:8]3[CH2:11][CH2:10][CH2:9]3)[C:12]=2[N:13]=1

Participants

5

Reactant 1

HCID 86623407HCID 86623407, compound

Product 1

HCID 86346256HCID 86346256, compoundYield 66.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1.7 g (0.0052 mole) of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclobutyl-amino]-propanoic acid ethyl ester (IV-23) in 10 mL of ethyl acetate was added over 1 hour to a suspension of 3.5 g (0.016 mole) of stannous chloride dihydrate in 12 mL of ethyl acetate and 1 mL of hydrochloric acid at ambient temperature. The mixture was stirred for additional hour and then diluted with 30 mL of water, and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with hexanes-ethyl acetate (80:20-0:100) to give 0.87 g of 2-chloro-9-cyclobutyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-23)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexanes-ethyl acetate (80:20-0:100)

Sources & evidence

ORD record
ord-2dd390413cc4469f8c2365d54de61f33
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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