Ethanol → HCID 87617706, compound

HRID 2111365Notes

Reaction equation

HRID 2111365 reaction equation
C(O)C.C([O:6][C:7](=O)[CH:8]([CH3:23])[CH:9]([N:11]([C:15]1[C:20]([NH2:21])=[CH:19][N:18]=[C:17]([Cl:22])[N:16]=1)[CH:12]1[CH2:14][CH2:13]1)[CH3:10])C>C(O)(=O)C>[Cl:22][C:17]1[N:18]=[CH:19][C:20]2[NH:21][C:7](=[O:6])[CH:8]([CH3:23])[CH:9]([CH3:10])[N:11]([CH:12]3[CH2:14][CH2:13]3)[C:15]=2[N:16]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 87618831HCID 87618831, compound

Product 1

HCID 87617706HCID 87617706, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50 mL of ethanol, 1 mL of acetic acid and 0.616 g of the (rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-cyclopropyl-amino]-2-methyl-butyric acid ethyl ester (V-46), 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 0.468 g of (rac)-2-chloro-9-cyclopropyl-7,8-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-46).

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-878247941bea40daadae6d034ad11054
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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