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

HRID 2111349Notes

Reaction equation

HRID 2111349 reaction equation
C(O)C.C([O:8][C:9](=O)[CH2:10][CH2:11][N:12]([C:16]1[C:21]([NH2:22])=[CH:20][N:19]=[C:18]([Cl:23])[N:17]=1)[CH:13]([CH3:15])[CH3:14])(C)(C)C>C(O)(=O)C>[Cl:23][C:18]1[N:19]=[CH:20][C:21]2[NH:22][C:9](=[O:8])[CH2:10][CH2:11][N:12]([CH:13]([CH3:15])[CH3:14])[C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 866234143-[(5-Amino-2-chloro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester

Product 1

HCID 866234152-Chloro-9-isopropyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneYield 79.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50 mL of ethanol, 1 mL of acetic acid and 1.4 g of the 3-[(5-amino-2-chloro-pyrimidin-4-yl)-isopropyl-amino]-propanoic acid tert-butyl ester (V-43), 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 0.85 g of 2-chloro-9-isopropyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-43).

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-b72c9b79dc8b419a9fd0c0dd07a1ab84
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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