Ethanol → 9-Butyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 2111355Notes

Reaction equation

HRID 2111355 reaction equation
C(O)C.C([O:8][C:9](=O)[CH2:10][CH2:11][N:12]([C:17]1[C:22]([NH2:23])=[CH:21][N:20]=[C:19]([Cl:24])[N:18]=1)[CH2:13][CH2:14][CH2:15][CH3:16])(C)(C)C>C(O)(=O)C>[CH2:13]([N:12]1[CH2:11][CH2:10][C:9](=[O:8])[NH:23][C:22]2[CH:21]=[N:20][C:19]([Cl:24])=[N:18][C:17]1=2)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 702EthanolHCID 86623417HCID 86623417, compound

Product 1

HCID 866234189-Butyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneYield 89.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50 mL of ethanol, 1 mL of acetic acid and 1.3 g of the 3-[(5-amino-2-chloro-pyrimidin-4-yl)-butyl-amino]-propionic acid tert-butyl ester (V-44), prepared in the previous step, was heated at reflux overnight, and then concentrated under reduced pressure. The residue was taken up in dichloromethane and washed successively with 10% sodium bicarbonate solution, water and then dried over anhydrous sodium sulfate. The mixture was filtered and then concentrated under reduced pressure. Trituration of the residue with ether, provided 0.90 g of 9-butyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-44).

Workup

  1. customprepared in the previous step
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. concentrationconcentrated under reduced pressure
  5. washwashed successively with 10% sodium bicarbonate solution, water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-218715330f414e10907127d9ca798534
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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